Organic Electroluminescent Element, Material for Organic Electroluminescent Element, Light Emitting Device, Display Device and Lighting Device Each Using Said Element, and Compound Used for Said Element

ABSTRACT

This application relates, in part, to an organic electroluminescent element including a substrate, a pair of electrodes including an anode and a cathode, disposed on the substrate, and at least one organic layer including a light emitting layer, disposed between the electrodes, in which at least one layer of the organic layer(s) contains a compound represented by the following formula (1). The organic electroluminescent element has low driving voltage and excellent durability. 
     
       
         
         
             
             
         
       
         
         
           
             wherein X 1  to X 11  represent CR 0  or N, and R 0  represents a hydrogen atom or a substituent. Adjacent two of X 1  to X 11  each independently represent at least CR 0 , R 0 s of the adjacent two CR 0 s are bonded to each other to form a ring, and only one R 0  of the adjacent two CR 0 s represents an aryl group or a heteroaryl group.

TECHNICAL FIELD

The present invention relates to an organic electroluminescent element,a material for an organic electroluminescent element, a light emittingdevice, a display device, and an illumination device each using theelement, and a compound used in the element.

BACKGROUND ART

Since organic electroluminescent elements (which may hereinafter also bereferred to as “elements” or “organic EL elements”) are capable ofhigh-luminance light emitting with driving at a low voltage, they havebeen actively researched and developed. The organic electroluminescentelements have organic layers between a pair of electrodes, and utilize,for light emitting, energy of an exciton generated as a result ofrecombination of electrons injected from a cathode and holes injectedfrom an anode in the organic layer.

In recent years, by using phosphorescent light emitting materials, theefficiency of organic electroluminescent elements is being enhanced. Forpractical use, however, improvements are required in terms of reductionin driving voltage, durability, and the like.

Meanwhile, an organic electroluminescent element which uses, as a hostmaterial of the light emitting layer, a compound having a structureobtained from triphenylamine by allowing the phenyl groups therein to beconnected to each other to undergo ring fusion, and thus, form acarbazole ring, has been known.

PTL 1 describes an organic electroluminescent element, which uses acompound of a structure obtained from triphenylamine by allowing two orthree phenyl groups therein to be connected to each other to undergoring fusion as a host material of the light emitting layer, and iscombined with a phosphorescent light emitting material. Further, it canbe seen from Examples in this document that the element is excellent indriving voltage and luminous efficiency.

On the other hand, PTL 2 describes a polycyclic fused compound furtherhaving a fused ring in a carbazole ring, and also describes that thecompound is used in an organic electroluminescent element. However, thedocument does not describe a compound of a fused structure obtained fromtriphenylamine by allowing two or more phenyl groups therein to beconnected to each other to undergo ring fusion.

PTL 3 describes a compound of a fused structure obtained fromtriphenylamine by allowing two phenyl groups therein to be connected toeach other to undergo ring fusion, and also describes that an organicelectroluminescent element having good luminous efficiency and lowdriving voltage can be provided by using the compound as a host materialof a light emitting layer.

CITATION LIST Patent Literature

-   [PTL 1] WO2011/042107-   [PTL 2] WO2010/131855-   [PTL 3] JP-A-2010-087496

SUMMARY OF INVENTION Technical Problem

In view of the above description, the present inventors have conductedstudies on the characteristics of the organic electroluminescentelements described in PTLs 1 to 3, and as a result, they have found thatthe elements of the PTLs 1 to 3 were not satisfactory in the reductionin driving voltage and also not satisfactory in durability.

It is an object of the present invention to provide an organicelectroluminescent element which has low driving voltage and excellentdurability by solving the aforementioned problems.

Solution to Problem

The present inventors have conducted extensive investigations, and as aresult, they have found that an organic electroluminescent elementhaving low driving voltage and excellent durability is provided by usinga compound obtained by allowing aryl groups or heteroaryl groups of two6-membered rings of an amine tri-substituted with aryl groups orheteroaryl groups of a 6-membered ring to be connected to each other toundergo ring fusion, and having aryl groups or heteroaryl groups as asubstituent, in which the substituents are fused at a specific position.

That is, the present invention which is a specific means for solving theproblem described above is as follows.

[1] An organic electroluminescent element including a substrate, a pairof electrodes including an anode and a cathode, disposed on thesubstrate, and at least one organic layer including a light emittinglayer, disposed between the electrodes,

in which at least one layer of the organic layer(s) contains a compoundrepresented by the following general formula (1).

(In the general formula (1), X¹ to X¹¹ each independently represent CR⁰or N, and R⁰s each independently represent a hydrogen atom or asubstituent. Adjacent two of X¹ to X¹¹ each independently represent atleast CR⁰, R⁰s of the adjacent two CR⁰s are bonded to each other to forma ring, and only one R⁰ of the adjacent two CR⁰s represents an arylgroup or a heteroaryl group. However, in the case where X⁷ and X⁸ eachindependently represent CR⁰, R⁰ contained in X⁷ and R⁰ contained in X⁸are not bonded to each other to form a ring.)

[2] In the organic electroluminescent element as described in [1], inthe general formula (1), one R⁰ of the adjacent two CR⁰s, in which R⁰sare bonded to each other to form a ring, preferably represents an arylgroup or a heteroaryl group of a 6-membered ring.

[3] In the organic electroluminescent element as described in [1] or[2], the compound represented by the general formula (1) is preferably acompound represented by any one of the following general formulae (2) to(9).

(In the general formulae (2) to (9), Y^(A1) to Y^(H1) each independentlyrepresent CR¹R², NR³, O, S, or Se, R¹ to R³ each independently representa substituent, X^(A1) to X^(A15), X^(B1) to X^(B15), X^(C1) to X^(C15),X^(D1) to X^(D15), X^(E1) to X^(E15), X^(F1) to X^(F15), X^(G1) toX^(G15) and X^(H1) to X^(H15) each independently represent CR⁴ or N, andCR⁴s each independently represent a hydrogen atom or a substituent.)

[4] In the organic electroluminescent element as described in [1] or[2], the compound represented by the general formula (1) is preferably acompound represented by any one of the following general formulae (10)to (17).

(In the general formulae (10) to (17), Y^(A1) to Y^(H1) eachindependently represent CR¹R², NR³, O, S, or Se, and R¹ to R³ eachindependently represent a substituent. R^(A1) to R^(A15), R^(B1) toR^(B15), R^(C1) to R^(C15), R^(D1) to R^(D15). R^(E1) to R^(E15), R^(F1)to R^(F15), R^(G1) to R^(G15) and R^(H1) to R^(H15) each independentlyrepresent a hydrogen atom or a substituent.)

[5] In the organic electroluminescent element as described in any one of[1] to [4], the value of LUMO of the compound represented by the generalformula (1), as determined by an electron density functional theory(B3LYP/6-31G (d) level), is preferably more than 1.25.

[6] In the organic electroluminescent element as described in any one of[1] to [5], the compound represented by the general formula (1)preferably has a substituent containing at least one of a pyridine ring,a pyrimidine ring, a triazine ring, a cyano group, and a carbonyl group.

[7] In the organic electroluminescent element as described in any one of[1] to [6], the light emitting layer preferably contains at least onekind of phosphorescent light emitting material.

[8] In the organic electroluminescent element as described in any one of[1] to [6], the phosphorescent light emitting material is preferably aniridium complex represented by the following general formula (E-1).

(In the general formula (E-1), Z¹ and Z² each independently represent acarbon atom or a nitrogen atom.

A¹ represents an atomic group that forms a 5- or 6-membered hetero ringtogether with Z¹ and a nitrogen atom.

B¹ represents an atomic group that forms a 5- or 6-membered ringtogether with Z² and a carbon atom.

(X—Y) represents a mono-anionic bidentate ligand.

n_(E1) represents an integer of 1 to 3.)

[9] In the organic electroluminescent element as described in [8], theiridium complex represented by the general formula (E-1) is preferablyrepresented by the following general formula (E-2).

(In the general formula (E-2), A^(E1) to A^(E8) each independentlyrepresents a nitrogen atom or C—R^(E).

R^(E) represents a hydrogen atom or a substituent.

(X—Y) represents a mono-anionic bidentate ligand.

n_(E2) represents an integer of 1 to 3.)

[10] In the organic electroluminescent element as described in any oneof [1] to [9], the light emitting layer preferably contains the compoundas described in any one of [1] to [6].

[11] A light emitting device using the organic electroluminescentelement as described in any one of [1] to [10].

[12] A display device using the organic electroluminescent element asdescribed in any one of [1] to [10].

[13] An illumination device using the organic electroluminescent elementas described in any one of [1] to [10].

[14] A compound represented by the following general formula (1).

(In the general formula (1), X¹ to X¹¹ each independently represent CR⁰or N, and R⁰s each independently represent a hydrogen atom or asubstituent. Adjacent two of X¹ to X¹¹ each independently represent atleast CR⁰, R⁰s of the adjacent two CR⁰s are bonded to each other to forma ring, and only one R⁰ of the adjacent two CR⁰s represents an arylgroup or a heteroaryl group. However, in the case where X⁷ and X⁸ eachindependently represent CR⁰, R⁰ contained in X⁷ and R⁰ contained in X⁸are not bonded to each other to form a ring.)

[15] The compound as described in [14] is preferably represented by anyone of the following general formulae (2) to (9).

(In the general formulae (2) to (9), Y^(A1) to Y^(H1) each independentlyrepresent CR¹R², NR³, O, S, or Se, and R¹ to R³ each independentlyrepresent a substituent. X^(A1) to X^(A15), X^(B1) to X^(B15), X^(C1) toX^(C15), X^(D1) to X^(D15), X^(E1) to X^(E15), X^(F1) to X^(F15), X^(G1)to X^(G15) and X^(H1) to X^(H15) each independently represent CR⁴ or N,and CR⁴s each independently represent a hydrogen atom or a substituent.)

[16] The compound as described in [14] or [15] is preferably representedby any one of the following general formulae (10) to (17).

(In the general formulae (10) to (17), Y^(A1) to Y^(H1) eachindependently represent CR^(I)R², NR³, O, S, or Se, and R¹ to R³ eachindependently represent a substituent. R^(A1) to R^(A15), R^(B1) toR^(B15), R^(C1) to R^(C15), R^(D1) to R^(D15), R^(E1) to R^(E15), R^(F1)to R^(F15), R^(G1) to R^(G15) and R^(H1) to R^(H15) each independentlyrepresent a hydrogen atom or a substituent.)

[17] A material for an organic electroluminescent element, representedby the following general formula (1).

(In the general formula (1), X¹ to X¹¹ each independently represent CR⁰or N, and R⁰s each independently represent a hydrogen atom or asubstituent. Adjacent two of X¹ to X¹¹ each independently represent atleast CR⁰, R⁰s of the adjacent two CR⁰s are bonded to each other to forma ring, and only one R⁰ of the adjacent two CR⁰s represents an arylgroup or a heteroaryl group. However, in the case where X⁷ and X⁸ eachindependently represent CR⁰, R⁰ contained in X⁷ and R⁰ contained in X⁸are not bonded to each other to form a ring.)

[18] The material for an organic electroluminescent element as describedin [17] is preferably represented by any one of the following generalformulae (2) to (9).

(In the general formulae (2) to (9), Y^(A1) to Y^(H1) each independentlyrepresent CR¹R², NR³, O, S, or Se, and R¹ to R³ each independentlyrepresent a substituent. X^(A1) to X^(A15), X^(B1) to X^(B15) X^(C1) toX^(C15), X^(D1) to X^(D15), X^(E1) to X^(E15), X^(F1) to X^(F15), X^(G1)to X^(G15) and X^(H1) to X^(H15) each independently represent CR⁴ or N,and CR⁴s each independently represent a hydrogen atom or a substituent.)

[19] The material for an organic electroluminescent element as describedin [17] or [18] is preferably represented by any one of the followinggeneral formulae (10) to (17).

(In the general formula (10) to (17), Y^(A1) to Y^(H1) eachindependently represent CR¹R², NR³, O, S, or Se, and R¹ to R³ eachindependently represent a substituent. R^(A1) to R^(A15), R^(B1) toR^(B15), R^(C1) to R^(C15), R^(D1) to R^(D15), R^(E1) to R^(E15), R^(F1)to R^(F15), R^(G1) to R^(G15) and R^(H1) to R^(H15) each independentlyrepresent a hydrogen atom or a substituent.)

Advantageous Effects of Invention

According to the present invention, an organic electroluminescentelement having low driving voltage and excellent durability can beprovided.

In addition, according to the present invention, a light emittingdevice, a display device, and an illumination device each using theorganic electroluminescent element can also be provided.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 is a schematic view showing one example of the configuration ofan organic electroluminescent element according to the presentinvention.

FIG. 2 is a schematic view showing one example of a light emittingdevice according to the present invention.

FIG. 3 is a schematic view showing one example of an illumination deviceaccording to the present invention.

DESCRIPTION OF EMBODIMENTS

Hereinbelow, the details of the present invention will be described. Thedescription of the configuration requirements as described below may bebased on representative embodiments of the present invention, but thepresent invention is not limited to these embodiments. Incidentally, inthe present specification, the range expressed with “to” means a rangeincluding the numerical values before and after “to” as the lower limitand the upper limit, respectively. [Organic Electroluminescent Element,Compound, and Material for Organic Electroluminescent Element]

The compound of the present invention and the material for an organicelectroluminescent element of the present invention may be representedby the general formula (1).

The organic electroluminescent element of the present invention mayinclude a substrate, a pair of electrodes including an anode and acathode, disposed on the substrate, and at least one organic layerincluding a light emitting layer, disposed between the electrodes, inwhich at least one layer of the organic layer(s) may contain thecompound represented by the general formula (1).

The configuration of the organic electroluminescent element of thepresent invention is not particularly limited. FIG. 1 shows an exampleof the configuration of the organic electroluminescent element of thepresent invention. An organic electroluminescent element 10 in FIG. 1includes organic layers between a pair of electrodes (an anode 3, and acathode 9) on a substrate 2.

The element configuration, and the substrate, the anode, and the cathodeof the organic electroluminescent element are described in detail, forexample, in JP-A-2008-270736, and the matters described in the patentpublication can be applied to the present invention.

Hereinafter, preferred embodiments of the organic electroluminescentelement of the present invention will be described, in the order of thesubstrate, the electrode, the organic layer, the protective layer, thesealing enclosure, the driving method, the light emitting wavelength,and applications thereof.

<Substrate>

The organic electroluminescent element of the present invention has asubstrate.

The substrate used in the present invention is preferably a substratethat does not scatter or decay light emitted from the organic layer. Inthe case of an organic material, those having excellent heat resistance,dimensional stability, solvent resistance, electrical insulatingproperties, and processability are preferred.

<Electrodes>

The organic electroluminescent element of the present invention has apair of electrodes including an anode and a cathode, disposed on thesubstrate.

In view of the properties of the light emitting element, at least oneelectrode of a pair of electrodes, the anode and the cathode, ispreferably transparent or semi-transparent.

(Anode)

The anode may be typically one having a function as an electrode ofsupplying holes into an organic layer, and is not particularly limitedin its shape, structure, size, or the like. Further, depending on theuse and purpose of the light emitting element, the anode can be suitablyselected from the known electrode materials. As described above, theanode is usually provided as a transparent anode.

(Cathode)

The cathode may be typically one having a function as an electrode ofinjecting electrons to an organic layer, and is not particularly limitedin its shape, structure, size, or the like. Further, depending on theuse and purpose of the light emitting element, the cathode can besuitably selected from the known electrode materials.

<Organic Layer>

The organic electroluminescent element of the present invention includesorganic layers disposed between the electrodes, in which the organiclayer(s) contains the compound represented by the general formula (1).

The organic layer is not particularly limited and can be suitablyselected depending on the use and purpose of the organicelectroluminescent element. However, the organic layer is preferablyformed on the transparent electrode or the semi-transparent electrode.In that case, the organic layer is formed on the whole surface or onesurface of the transparent electrode or the semi-transparent electrode.

The shape, the size, the thickness, and the like of the organic layerare not particularly limited and can be suitably selected depending onthe purpose.

Hereinafter, the configuration of the organic layer, the method forforming an organic layer, preferred aspects of the respective layersconstituting the organic layer, and the materials used in the respectivelayers in the organic electroluminescent element of the presentinvention will be described in detail in order.

(Configuration of Organic Layers)

In the organic electroluminescent element of the present invention, theorganic layers preferably include a charge transporting layer. Thecharge transporting layer means a layer, in which charge transfer occurswhen a voltage is applied to the organic electroluminescent element.Specific examples of the charge transporting layer include a holeinjecting layer, a hole transporting layer, an electron blocking layer,a light emitting layer, a hole blocking layer, an electron transportinglayer, and an electron injecting layer.

The organic electroluminescent element of the present invention includesa light emitting layer containing a phosphorescent light emittingmaterial and other organic layers, the light emitting layer preferablycontaining a compound represented by the general formula (1). Here, theplace where the compound represented by the general formula (1) isincluded is not particularly limited, but the light emitting layerpreferably contains the compound represented by the general formula (1).Here, the compound represented by the general formula (1) is preferablyused as a host compound of the light emitting layer. In addition, in theorganic electroluminescent element of the present invention, the organiclayers preferably include a light emitting layer containing thephosphorescent light emitting material and other organic layers. In theorganic electroluminescent element of the present invention, however,even when the organic layers include a light emitting layer and otherorganic layers, the layers are not required to be clearly distinguishedfrom one another.

Furthermore, preferably the organic electroluminescent element of thepresent invention has an electron transporting layer adjacent to thecathode between the pair of electrodes, optionally has an hole blockinglayer adjacent to the cathode of the electron transporting layer, andthe electron transporting layer or the hole blocking layer preferablycontains the compound represented by the general formula (1).

Each of these organic layers may include a plurality of layers, and inthe case of providing a plurality of layers, the layers may be formedfrom the same material or may be formed from different materials forrespective layers.

(Method for Forming Organic Layer)

The respective organic layers in the organic electroluminescent elementof the present invention can be suitably formed by any of dry filmforming methods such as a deposition method and a sputtering method, andwet type film formation methods (solution coating methods) such as atransfer method, a printing method, a spin coating method, and a barcoating method.

In the organic electroluminescent element of the present invention, theorganic layer disposed on the pair of electrodes preferably includes atleast a layer formed by the deposition of a composition furtherincluding the compound represented by the general formula (1).

(Light Emitting Layer)

The light emitting layer is a layer having a function of, uponapplication of an electric field, receiving holes from the anode, thehole injecting layer or the hole transporting layer, receiving electronsfrom the cathode, the electron injecting layer or the electrontransporting layer, providing a recombination site of the holes and theelectrons, and thereby causing light emitting. However, the lightemitting layer in the present invention is not necessarily limited tothe light emitting by such a mechanism. The light emitting layer in theorganic electroluminescent element of the present invention preferablycontains at least one kind of phosphorescent light emitting material.

The light emitting layer in the organic electroluminescent element ofthe present invention may be constituted of only the phosphorescentlight emitting material, or may be constituted as a mixed layer of ahost material and the phosphorescent light emitting material. One kindor two or more kinds of phosphorescent light emitting materials may beused. The host material is preferably a charge transporting material.One kind or two or more kinds of materials may be used as the hostmaterial. Examples thereof include a configuration in which an electrontransporting host material and a hole transporting host material aremixed. In addition, the light emitting layer may contain a materialwhich does not have charge transporting property and does not emitlight.

In addition, the light emitting layer may be made of a single layer ormultiple layers including two or more layers. The layers may include thesame light emitting material or host material, or also may includedifferent materials for the respective layers. In the case where aplurality of light emitting layers are present, the light emittinglayers may emit light in different luminous colors from one another.

The thickness of the light emitting layer is not particularly limited,but it is usually from 2 nm to 500 nm, and above all, from the viewpointof external quantum efficiency, it is more preferably from 3 nm to 200nm, and still more preferably from 5 nm to 100 nm.

In the organic electroluminescent element of the present invention, in apreferred embodiment, the light emitting layer preferably contains acompound represented by the general formula (1), and in a more preferredembodiment, the compound represented by the general formula (1) is usedas a host material of the light emitting layer. Here, the host materialas referred to in the present specification is a compound which chieflyplays a role in injecting or transporting charges in the light emittinglayer and is also a compound which does not substantially emit light initself. As used herein, it is meant by the terms “which does notsubstantially emit light” that the amount of light emission from thecompound which does not substantially emit light is preferably 5% orless, more preferably 3% or less, and still more preferably 1% or less,with respect to the total amount of light emission in the whole of theelement.

Hereinafter, as the materials of the light emitting layer, the compoundrepresented by the general formula (1), the phosphorescent lightemitting material, and host materials other than the compoundrepresented by the general formula (1) will be described in this order.Further, the compound represented by the general formula (1) may be usedas a material other than the light emitting layer in the organicelectroluminescent element of the present invention.

(1) Compound Represented by General Formula (1)

It is reported that the phenylcarbazole described in WO2010/131855 andthe like has cleavage of a bond between N of carbazole and C of a phenylgroup cleaved, as a result of the analysis of decomposed products afterelement deterioration (J. Appl. Phys. 2007, 101, 024512). Meanwhile, acompound having an indolocarbazole skeleton represented by the followinggeneral formula (1), or a skeleton formed by substituting a specificposition of a carbon atom in the indolocarbazole skeleton with anitrogen atom can increase the durability of the obtained organicelectroluminescent element. Not wishing to be restricted to any reason,the present inventors have contemplated that as suggested by the abovearticles, a cause of deteriorating the durability consists in the bondcleavage of the cause of deteriorating the durability, and a compoundhaving an indolocarbazole skeleton represented by the following generalformula (1), or a skeleton formed by substituting a specific position ofa carbon atom in the indolocarbazole skeleton with a nitrogen atom hashigh durability by inhibiting the bond cleavage or promoting therebonding after the bond cleavage.

Here, indolocarbazole compounds that have been well-known in the relatedart did not have an additional fused ring in indolocarbazole. Such theindolocarbazole compounds have a high ionization potential (=a highvalue of HOMO), and a hole injection barrier from a hole transportinglayer is high, and thus, has not yet reached an element driving voltageat a level for practical use. In the present invention, by subjecting acompound having an indolocarbazole skeleton and a compound having askeleton formed by substituting a specific position of a carbon atom inthe indolocarbazole skeleton to ring fusion on a π plane, the elementdriving voltage can be reduced, as compared with indolocarbazole havingno fused ring. Not wishing to be restricted to any reason, it iscontemplated that it is possible to decrease the ionization potential(=to decrease value of HOMO), and as a result, a hole injection barrierfrom a hole transporting layer has been alleviated.

In addition, for the compound having an indolocarbazole skeletondescribed in WO2011/042107 and JP-A-2010-087496, there is a descriptionthat the indolocarbazole skeleton is further fused, but there is noexemplification of the specific compounds, and since there is a problemin the number of ring members constituting the skeleton and thepositions of the fused rings, it can be seen that it is difficult tosatisfy both of durability and reduction in a driving voltage.

A compound represented by the following general formula (1) will bedescribed below.

(In the general formula (1), X¹ to X¹¹ each independently represent CR⁰or N, and R⁰s each independently represent a hydrogen atom or asubstituent. Adjacent two of X¹ to X¹¹ each independently represent atleast CR⁰, R⁰s of the adjacent two CR⁰s are bonded to each other to forma ring, and only one R⁰ of the adjacent two CR⁰s represents an arylgroup or a heteroaryl group. However, in the case where X⁷ and X⁸ eachindependently represent CR⁰, R⁰ contained in X⁷ and R⁰ contained in X⁸are not bonded to each other to form a ring.)

Incidentally, in the present invention, the hydrogen atoms in thedescription of the general formula (1) include isotopes (a deuteriumatom and the like), and any atoms constituting the further substituentalso include the isotopes thereof.

In the present invention, when referring to a “substituent”, thesubstituent may be further substituted. For example, when the “alkylgroup” is referred to in the present invention, it includes an alkylgroup substituted with a fluorine atom (for example, a trifluoromethylgroup) and an alkyl group substituted with an aryl group (for example, atriphenylmethyl group), but when “an alkyl group having 1 to 6 carbonatoms” is referred to herein, it represents any of alkyl groups having 1to 6 carbon atoms, including the alkyl groups which are substituted.

In the general formula (1), X¹ to X¹¹ each independently represent CR⁰or N, and R⁰s each independently represent a hydrogen atom or asubstituent.

In the general formula (1), examples of the substituent represented byR⁰ each independently the following Substituent Group A, the substituentmay have an additional substituent, and examples of the additionalsubstituent include the groups selected from the Substituent Group A.

<<Substituent Group A>>

An alkyl group (preferably having 1 to 30 carbon atoms, more preferablyhaving 1 to 20 carbon atoms, and particularly preferably having 1 to 10carbon atoms, for example, methyl, ethyl, n-propyl, isopropyl, t-butyl,n-octyl, n-hexyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, andcyclohexyl), an alkenyl group (preferably having 2 to 30 carbon atoms,more preferably having 2 to 20 carbon atoms, and particularly preferablyhaving 2 to 10 carbon atoms, for example, vinyl, allyl, 2-butenyl, and3-pentenyl), an alkynyl group (preferably having 2 to 30 carbon atoms,more preferably having 2 to 20 carbon atoms, and particularly preferablyhaving 2 to 10 carbon atoms, for example, propargyl and 3-pentynyl), anaryl group (preferably having 6 to 30 carbon atoms, more preferablyhaving 6 to 20 carbon atoms, and particularly preferably having 6 to 14carbon atoms, for example, phenyl, p-methylphenyl, naphthyl, andanthranyl), amino group (preferably having 0 to 30 carbon atoms, morepreferably having 0 to 20 carbon atoms, and particularly preferablyhaving 0 to 10 carbon atoms, for example, amino, methylamino,dimethylamino, diethylamino, dibenzylamino, phenylamino, diphenylamino,and ditolylamino), an alkoxy group (preferably having 1 to 30 carbonatoms, more preferably having 1 to 20 carbon atoms, and particularlypreferably having 1 to 10 carbon atoms, for example, methoxy, ethoxy,butoxy, and 2-ethylhexyloxy), and aryloxy group (preferably having 6 to30 carbon atoms, more preferably having 6 to 20 carbon atoms, andparticularly preferably having 6 to 12 carbon atoms, for example,phenyloxy, 1-naphthyloxy, and 2-naphthyloxy), a heterocyclic oxy group(preferably having 1 to 30 carbon atoms, more preferably having 1 to 20carbon atoms, and particularly preferably having 1 to 12 carbon atoms,for example, pyridyloxy, pyrazyloxy, pyrimidyloxy, and quinolyloxy), anacyl group (preferably having 2 to 30 carbon atoms, more preferablyhaving 2 to 20 carbon atoms, and particularly preferably having 2 to 12carbon atoms, for example, acetyl, benzoyl, formyl, and pivaloyl), analkoxycarbonyl group (preferably having 2 to 30 carbon atoms, morepreferably having 2 to 20 carbon atoms, and particularly preferablyhaving 2 to 12 carbon atoms, for example, methoxycarbonyl andethoxycarbonyl), an aryloxycarbonyl group (preferably having 7 to 30carbon atoms, more preferably having 7 to 20 carbon atoms, andparticularly preferably having 7 to 12 carbon atoms, for example,phenyloxycarbonyl), an acyloxy group (preferably having 2 to 30 carbonatoms, more preferably having 2 to 20 carbon atoms, and particularlypreferably having 2 to 10 carbon atoms, for example, acetoxy andbenzoyloxy), an acylamino group (preferably having 2 to 30 carbon atoms,more preferably having 2 to 20 carbon atoms, and particularly preferablyhaving 2 to 10 carbon atoms, for example, acetylamino and benzoylamino),an alkoxycarbonylamino group (preferably having 2 to 30 carbon atoms,more preferably having 2 to 20 carbon atoms, and particularly preferablyhaving 2 to 12 carbon atoms, for example, methoxycarbonylamino), anaryloxycarbonylamino group (preferably having 7 to 30 carbon atoms, morepreferably having 7 to 20 carbon atoms, and particularly preferablyhaving 7 to 12 carbon atoms, for example, phenyloxycarbonylamino), asulfonylamino group (preferably having 1 to 30 carbon atoms, morepreferably having 1 to 20 carbon atoms, and particularly preferablyhaving 1 to 12 carbon atoms, for example, methanesulfonylamino andbenzenesulfonylamino), a sulfamoyl group (preferably having 0 to 30carbon atoms, more preferably having 0 to 20 carbon atoms, andparticularly preferably having 0 to 12 carbon atoms, for example,sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, and phenylsulfamoyl), acarbamoyl group (preferably having 1 to 30 carbon atoms, more preferablyhaving 1 to 20 carbon atoms, and particularly preferably having 1 to 12carbon atoms, for example, carbamoyl, methylcarbamoyl, diethylcarbamoyl,and phenylcarbamoyl), an alkylthio group (preferably having 1 to 30carbon atoms, more preferably having 1 to 20 carbon atoms, andparticularly preferably having 1 to 12 carbon atoms, for example,methylthio and ethylthio), an arylthio group (preferably having 6 to 30carbon atoms, more preferably having 6 to 20 carbon atoms, andparticularly preferably having 6 to 12 carbon atoms, for example,phenylthio), a heterocyclic thio group (preferably having 1 to 30 carbonatoms, more preferably having 1 to 20 carbon atoms, and particularlypreferably having 1 to 12 carbon atoms, for example, pyridylthio,2-benzoimizolylthio, 2-benzoxazolylthio, and 2-benzothiazolylthio), asulfonyl group (preferably having 1 to 30 carbon atoms, more preferablyhaving 1 to 20 carbon atoms, and particularly preferably having 1 to 12carbon atoms, for example, mesyl and tosyl), a sulfinyl group(preferably having 1 to 30 carbon atoms, more preferably having 1 to 20carbon atoms, and particularly preferably having 1 to 12 carbon atoms,for example, methanesulfinyl and benzenesulfinyl), a ureido group(preferably having 1 to 30 carbon atoms, more preferably having 1 to 20carbon atoms, and particularly preferably having 1 to 12 carbon atoms,for example, ureido, methylureido, and phenylureido), phosphoramidegroup (preferably having 1 to 30 carbon atoms, more preferably having 1to 20 carbon atoms, and particularly preferably having 1 to 12 carbonatoms, for example, diethylphosphoramide and phenylphosphoramide), ahydroxy group, a mercapto group, a halogen atom (for example, a fluorineatom, a chlorine atom, a bromine atom, and an iodine atom), a sulfogroup, a carboxyl group, a nitro group, a hydroxamic group, a sulfinogroup, a hydrazino group, an imino group, a heterocyclic group(inclusive of an aromatic heterocyclic group, which preferably has 1 to30 carbon atoms, and more preferably 1 to 12 carbon atoms and in whichexamples of the hetero atom include a nitrogen atom, an oxygen atom, asulfur atom, a phosphorus atom, a silicon atom, a selenium atom, and atellurium atom, and specific examples thereof include pyridyl,pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl,imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, quinolyl,furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino,morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl,benzothiazolyl, a carbazolyl group, an azepinyl group, and a silolylgroup), a silyl group (preferably having 3 to 40 carbon atoms, morepreferably having 3 to 30 carbon atoms, and particularly preferablyhaving 3 to 24 carbon atoms, for example, trimethylsilyl andtriphenylsilyl), a silyloxy group (preferably having 3 to 40 carbonatoms, more preferably having 3 to 30 carbon atoms, and particularlypreferably having 3 to 24 carbon atoms, for example, trimethylsilyloxyand triphenylsilyloxy), and a phosphoryl group (for example, adiphenylphosphoryl group and a dimethylphosphoryl group). Thesesubstituents may be further substituted, and examples of the additionalsubstituent include the groups selected from the Substituent Group A asdescribed above.

The R⁰s included in X¹ to X¹¹ each independently represent, among theSubstituent Group A, preferably a hydrogen atom, an aryl group, or aheteroaryl group, and more preferably a hydrogen atom or an aryl group.

The aryl group represented by R⁰ preferably has 6 to 30 carbon atoms,more preferably has 6 to 20 carbon atoms, and particularly preferablyhas 6 to 18 carbon atoms, and examples thereof include a phenyl group, axylyl group, a biphenyl group, a terphenyl group, a naphthyl group, ananthranyl group, and a triphenylenyl group.

The heteroaryl group represented by R⁰ preferably has 5 to 30 ringmembers, more preferably has 5 to 20 ring members, and particularlypreferably has 5 to 15 ring members, and examples thereof include apyridyl group, a pyrimidyl group, a triazyl group, a pyrazyl group, apyridazyl group, a carbazolyl group, a dibenzothiophenyl group, and adibenzofuranyl group.

R⁰ contained in X¹ to X¹¹ may have an additional substituent representedby the Substituent Group A, but in the case where R⁰ has the additionalsubstituent, the substituent is preferably an aryl group, or asubstituent containing at least one of a pyridine ring, a pyrimidinering, a triazine ring, a cyano group, and a carbonyl group. Above all,an unsubstituted aryl group, a pyridinyl group, a pyrimidinyl group, atriazinyl group, a cyano group-substituted aryl group, and anarylcarbonyl group-substituted aryl group are more preferred, aunsubstituted aryl group, a triazinyl group, and a cyanogroup-substituted aryl group are still preferable, and an unsubstitutedaryl group and a cyano group-substituted aryl group are particularlypreferred.

However, it is preferable that the additional substituents which may becontained in R⁰ be not connected to each other to form a fused ring,from the viewpoint of increasing the luminous efficiency of greenphosphorescent light.

The additional substituents which may be contained in R⁰ may be furthersubstituted. In the case where the additional substituents which may becontained in R⁰ are each a pyridinyl group, a pyrimidinyl group, or atriazinyl group, they are preferably all substituted with diaryl(preferably substituted with diphenyl).

Adjacent two of X¹ to X¹¹ each independently represent at least CR⁰, R⁰sof the adjacent two CR⁰s are bonded to each other to form a ring andonly one R⁰ of the adjacent two CR⁰s represents an aryl group or aheteroaryl group. However, in the case where X⁷ and X⁸ eachindependently represent CR⁰, R⁰ contained in X⁷ and R⁰ contained in X⁸are not bonded to each other to form a ring.

In the present invention, in the general formula (1), one R⁰ of theadjacent two CR⁰s, in which R⁰s are bonded to each other to form a ring,preferably represents an aryl group of a 6-membered ring (that is, aphenyl group) or an heteroaryl group of a 6-membered ring, and morepreferably a phenyl group.

In the present invention, in the general formula (1), the other R⁰ otherthan R⁰ representing an aryl group or a heteroaryl group, of theadjacent two CR⁰s, in which R⁰s are bonded to each other to form a ring,is not particularly limited as long as it is a substituent other than anaryl group or a heteroaryl group. Above all, the substituent ispreferably one which is bonded to R⁰ representing an aryl group or aheteroaryl group to form a ring which is a 5-membered ring, from theviewpoint of maintaining the luminous efficiency of green phosphorescentlight.

As the substituent which is bonded to R⁰ representing an aryl group or aheteroaryl group to form a ring which is a 5-membered ring, asubstituent which can form CR¹R², NR³ (R¹ to R³ each independentlyrepresent a substituent), O, S, or Se as a linking group having one ofan atom-linking chain length when forming a fused ring is preferred, asubstituent which can form CR¹R², NR³, O, or S is more preferred, asubstituent which can form O or S is particularly preferred, and asubstituent which can form O is more particularly preferred.

The number of CR⁰ s in X¹ to X¹¹ is from 2 to 11, preferably from 5 to11, more preferably from 8 to 11, particularly preferably from 9 to 11,more particularly preferably 10 or 11, and still more particularlypreferably 11.

Furthermore, the number of CR⁰ s in X¹ to X¹¹, in which R⁰ is asubstituent, inclusive of R⁰s in which R⁰s are bonded to each other toform a ring, is from 2 to 11, more preferably from 3 to 8, and stillmore preferably 3 or 4.

The position of CR⁰s in X¹ to X¹¹, in which R⁰ is a substituent, dependson the position of a ring formed by fusion of two CR⁰s, but it ispreferably at least one of X², X⁵ and X¹⁰, and more preferably at leasttwo of X², X⁵ and X⁰.

The combination of the positions of the adjacent two CR⁰s in X¹ to X¹¹,which are bonded to each other to form a ring, is not particularlylimited as long as it is not a combination of X¹ and X⁸, but acombination of X¹ and X², a combination of X² and X³, a combination ofX⁴ and X⁵, a combination of X⁵ and X⁶, a combination of X⁶ and X⁷, acombination of X⁸ and X⁹, a combination of X⁹ and X¹⁰, and a combinationof X¹⁰ and X¹¹ are preferred, and a combination of X¹ and X², acombination of X² and X³, a combination of X⁴ and X⁵, a combination ofX⁵ and X⁶, a combination of X⁹ and X¹⁰, and a combination of X¹⁰ and X¹¹are more preferred.

In the compound represented by the general formula (1), the number ofthe rings formed by the mutual bonding of the adjacent two CR⁰s in X¹ toX¹¹ is preferably from 1 to 3, and particularly preferably 1 from theviewpoint of remarkably increasing the luminous efficiency of greenphosphorescent light.

In the present invention, the compound represented by the generalformula (1) is preferably a compound represented by any one of thefollowing general formulae (2) to (9).

In the general formulae (2) to (9), Y^(A1) to Y^(H1) each independentlyrepresent CR¹R², NR³, O, S, or Se, and R¹ to R³ each independentlyrepresent a substituent.

X^(A1) to X^(A15), X^(B1) to X^(B15), X^(C1) to X^(C15), X^(D1) toX^(D15), X^(E1) to X^(E15), X^(F1) to X^(F15), X^(G1) to X^(G15) andX^(H1) to X^(H15) each independently represent CR⁴ or N, and CR⁴s eachindependently represent a hydrogen atom or a substituent.

In the general formula (2), Y^(A1) represents CR¹R², NR³, O, S, or Se,and R¹ to R³ each independently represent a substituent. The preferredrange of Y^(A1) is the same as the preferred range of the linking grouphaving one of an atom-linking chain length, shown when the other R⁰sother than R⁰ representing an aryl group or a heteroaryl group, of theadjacent two CR⁰s, in which R⁰s are bonded to each other to form a ring,form a fused ring in the general formula (1).

Examples of the substituents represented by substituents R¹ and R² oncarbon atoms include the Substituent Group A as described above, and thesubstituent on the carbon atom is preferably an alkyl group, aperfluoroalkyl group, an aryl group, a heteroaryl group, a dialkylaminogroup, a diarylamino group, an alkoxy group, a cyano group, or afluorine atom, more preferably an alkyl group or an aryl group, andparticularly preferably a methyl group or a phenyl group.

Examples of the substituent represented by R³ on the nitrogen atominclude the following Substituent Group B.

<<Substituent Group B>>

An alkyl group (preferably having 1 to 30 carbon atoms, more preferablyhaving 1 to 20 carbon atoms, and particularly preferably having 1 to 10carbon atoms, for example, methyl, ethyl, isopropyl, tert-butyl,n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, andcyclohexyl), an alkenyl group (preferably having 2 to 30 carbon atoms,more preferably having 2 to 20 carbon atoms, and particularly preferablyhaving 2 to 10 carbon atoms, for example, vinyl, allyl, 2-butenyl, and3-pentenyl), an alkynyl group (preferably having 2 to 30 carbon atoms,more preferably having 2 to 20 carbon atoms, and particularly preferablyhaving 2 to 10 carbon atoms, for example, propargyl and 3-pentynyl), anaryl group (preferably having 6 to 30 carbon atoms, more preferablyhaving 6 to 20 carbon atoms, and particularly preferably having 6 to 12carbon atoms, for example, phenyl, p-methylphenyl, naphthyl, andanthranyl), a cyano group, and a heterocyclic group (inclusive of anaromatic heterocyclic group, which preferably has 1 to 30 carbon atoms,and more preferably 1 to 12 carbon atoms and in which examples of thehetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, aphosphorus atom, a silicon atom, a selenium atom, and a tellurium atom,and specific examples thereof include pyridyl, pyrazinyl, pyrimidyl,pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl,thiazolyl, isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl,selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino,pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl, benzothiazolyl,a carbazolyl group, an azepinyl group, and a silolyl group). Thesesubstituents may be further substituted, and examples of the additionalsubstituent include the groups selected from the Substituent Group B asdescribed above.

The substituent represented by R³ on the nitrogen atom is preferably analkyl group, an aryl group, an aromatic hetero ring group, morepreferably an aryl group, and particularly preferably a phenyl group, ora phenyl group substituted with a phenyl group (biphenyl group).

Furthermore, the substituent represented by R³ of Y^(A1) on the nitrogenatom may be connected to X^(A15) to form a ring.

In the general formula (2), X^(A1) to X^(A15) each independentlyrepresent CR⁴ or N, and CR⁴s each independently represent a hydrogenatom or a substituent.

The preferred ranges of X^(A1) to X^(A11) are the same as the preferredranges of X¹ to X¹¹ in the general formula (1).

In the general formula (2), examples of the substituent represented byR⁴ in the case where X^(A12) to X^(A15) are CR⁴s each independentlyinclude the Substituent Group A, and the substituent may have anadditional substituent. Examples of the additional substituent includethe groups selected from the Substituent Group A. Above all, R⁴s areeach independently preferably a hydrogen atom, an aryl group, or aheteroaryl group in the Substituent Group A, and more preferably ahydrogen atom or an aryl group.

The aryl group represented by R⁴ preferably has 6 to 30 carbon atoms,more preferably has 6 to 20 carbon atoms, and particularly preferablyhas 6 to 18 carbon atoms, and examples thereof include a phenyl group, axylyl group, a biphenyl group, a terphenyl group, a naphthyl group, ananthranyl group, and a triphenylenyl group.

The heteroaryl group represented by R⁴ preferably has 5 to 30 ringmembers, more preferably has 5 to 20 ring members, and particularlypreferably has 5 to 15 ring members, and examples thereof include apyridyl group, a pyrimidyl group, a triazyl group, a pyrazyl group, apyridazyl group, a carbazolyl group, a dibenzothiophenyl group, and adibenzofuranyl group.

R⁴ contained in X^(A12) to X^(A15) may have an additional substituentrepresented by the Substituent Group A as described above. In the casewhere R⁴ has such an additional substituent, the substituent ispreferably substituent containing an aryl group, or at least one of apyridine ring, a pyrimidine ring, a triazine ring, a cyano group, and acarbonyl group. Above all, an aryl group-substituted aryl group is morepreferred, and the additional substituent which may be contained in R⁴is particularly preferably further substituted. R⁴ is preferably aphenyl group-substituted phenyl group (biphenyl group), or acyano-substituted, phenyl group-substituted, or aryl group-substitutedphenyl group.

The number of CR⁴s in X^(A12) to X^(A15) is preferably from 1 to 4, morepreferably from 2 to 4, particularly preferably 3 or 4, and moreparticularly preferably 4.

Furthermore, the number of CR⁴s in X^(A12) to X^(A15), in which R⁴ is asubstituent, is preferably 0 or 1, and more preferably 0.

The position of CR⁴s in X^(A12) to X^(A15), in which R⁴ is asubstituent, is preferably at least one of the positions adjacent toY^(A1) (the position of X^(A15) in the general formula (2)), and morepreferably only one of the positions adjacent to Y^(A1).

The general formula (2) is more preferably represented by the generalformula (10) as described later.

In the general formula (3), Y^(B1) represents CR¹R², NR³, O, S, or Se,and R¹ to R³ each independently represent a substituent. The preferredrange of Y^(B1) is the same as the preferred range of Y^(A1) in thegeneral formula (2).

Furthermore, the substituent represented by R³ of Y^(B1) on the nitrogenatom may be connected to X^(B1) or X^(B12) to form a ring.

In the general formula (3), X^(B1) to X^(B15) each independentlyrepresent CR⁴ or N, and CR⁴s each independently represent a hydrogenatom or a substituent. The preferred ranges of X^(B1) to X^(B15) are thesame as the preferred ranges of X^(A1) to X^(A15) in the general formula(2).

The preferred relationship between Y^(B1) and X^(B1) to X^(B15) in thegeneral formula (3) is the same as the preferred relationship betweenY^(A1) and X^(A1) to X^(A15) in the general formula (2), that is, theposition of CR⁴ in the case where X^(B12) to X^(B15) have CR⁴ as asubstituent is preferably a position adjacent to Y^(B1) (the position ofX^(B12) in the general formula (3)).

The general formula (3) is more preferably represented by the generalformula (11) as described later.

In the general formula (4), Y^(C1) represents CR¹R², NR³, O, S, or Se,and R¹ to R³ each independently represent a substituent. The preferredrange of Y^(C1) is the same as the preferred range of Y^(A1) in thegeneral formula (2).

Furthermore, the substituent represented by R³ of Y^(C1) on the nitrogenatom may be connected to X^(C6) or X^(c15) to form a ring.

In the general formula (4), X^(C1) to X^(C15) each independentlyrepresent CR⁴ or N, and CR⁴s each independently represent a hydrogenatom or a substituent. The preferred ranges of X^(C1) to X^(C15) are thesame as the preferred ranges of X^(A1) to X^(A15) in the general formula(2).

The preferred relationship between Y^(C1) and X^(c1) to X^(C15) in thegeneral formula (4) is the same as the preferred relationship betweenY^(A1) and X^(A1) to X^(A15) in the general formula (2), that is, theposition of CR⁴ in the case where X^(C12) to X^(C15) have CR⁴ as asubstituent is preferably a position adjacent to Y^(C1) (the position ofX^(C15) in the general formula (4)).

The general formula (4) is more preferably represented by the generalformula (12) as described later.

In the general formula (5), Y^(D1) represents CR¹R², NR³, O, S, or Se,and R¹ to R³ each independently represent a substituent. The preferredrange of Y^(D1) is the same as the preferred range of Y^(A1) in thegeneral formula (2).

Furthermore, the substituent on the nitrogen atom represented by R³ ofY^(D1) may be connected to X^(D12) to form a ring.

In the general formula (5), X^(D1) to X^(D15) each independentlyrepresent CR⁴ or N, and CR⁴s each independently represent a hydrogenatom or a substituent. The preferred ranges of X^(D1) to X^(D15) are thesame as the preferred ranges of X^(A1) to X¹⁵S in the general formula(2).

The preferred relationship between Y^(D1) and X^(D1) to X^(D15) in thegeneral formula (5) is the same as the preferred relationship betweenY^(A1) and X^(A1) to X^(A15) in the general formula (2), that is, theposition of CR⁴ in the case where X^(D12) to X^(D15) have CR⁴ as asubstituent is preferably a position adjacent to Y^(D1) (the position ofX^(D12) in the general formula (5)).

The general formula (5) is more preferably represented by the generalformula (13) as described later.

In the general formula (6), Y^(E1) represents CR¹R², NR³, O, S, or Se,and R¹ to R³ each independently represent a substituent. The preferredrange of Y^(E1) is the same as the preferred range of Y^(A1) in thegeneral formula (2).

Furthermore, the substituent represented by R³ of Y^(E1) on the nitrogenatom may be connected to X^(E7) or X^(E15) to form a ring.

In the general formula (6), X^(E1) to X^(E15) each independentlyrepresent CR⁴ or N, and CR⁴s each independently represent a hydrogenatom or a substituent. The preferred ranges of X^(E1) to X^(E15) are thesame as the preferred ranges of X^(A1) to X^(A15) in the general formula(2).

The preferred relationship between Y^(E1) and X^(E1) to X^(E15) in thegeneral formula (6) is the same as the preferred relationship betweenY^(A1) and X^(A1) to X^(A15) in the general formula (2), that is, theposition of CR⁴ in the case where X^(E12) to X^(E15) have CR⁴ as asubstituent is preferably a position adjacent to Y^(E1) (the position ofX^(E15) in the general formula (6)).

The general formula (6) is more preferably represented by the generalformula (14) as described later.

In the general formula (7), Y^(F1) represents CR¹R², NR³, O, S, or Se,and R¹ to R³ each independently represent a substituent. The preferredrange of Y^(F1) is the same as the preferred range of Y^(A1) in thegeneral formula (2).

Furthermore, the substituent represented by R³ of Y^(E1) on the nitrogenatom may be connected to X^(F1) or X^(F12) to form a ring.

In the general formula (7), X^(F1) to X^(F15) each independentlyrepresent CR⁴ or N, and CR⁴s each independently represent a hydrogenatom or a substituent. The preferred ranges of X^(F1) to X^(F15) are thesame as the preferred ranges of X^(A1) to X^(A15) in the general formula(2).

The preferred relationship between Y^(F1) and X^(F1) to X^(F15) in thegeneral formula (7) is the same as the preferred relationship betweenY^(A1) and X^(A1) to X^(A15) in the general formula (2), that is, theposition of CR⁴ in the case where X^(F12) to X^(F15) have CR⁴ as asubstituent is preferably a position adjacent to Y^(F1) (the position ofX^(F12) in the general formula (7)).

The general formula (7) is more preferably represented by the generalformula (15) as described later.

In the general formula (8), Y^(G1) represents CR¹R², NR³, O, S, or Se,and R¹ to R³ each independently represent a substituent. The preferredrange of Y^(G1) is the same as the preferred range of Y^(A1) in thegeneral formula (2).

Furthermore, the substituent represented by R³ of Y^(G1) on the nitrogenatom may be connected to X^(G15) to form a ring.

In the general formula (8), X^(G1) to X^(G15) each independentlyrepresent CR⁴ or N, and CR⁴s each independently represent a hydrogenatom or a substituent. The preferred ranges of X^(G1) to X^(G15) are thesame as the preferred ranges of X^(A1) to X^(A15) in the general formula(2).

The preferred relationship between Y^(G1) and X^(G1) to X^(G15) in thegeneral formula (8) is the same as the preferred relationship betweenY^(A1) and X^(A1) to X^(A15) in the general formula (2), that is, theposition of CR⁴ in the case where X^(G12) to X^(G15) have CR⁴ as asubstituent is preferably a position adjacent to Y^(G1) (the position ofX^(G15) in the general formula (8)).

The general formula (8) is more preferably represented by the generalformula (16) as described later.

In the general formula (9), Y^(H1) represents CR¹R², NR³, O, S, or Se,and R¹ to R³ each independently represent a substituent. The preferredrange of Y^(H1) is the same as the preferred range of Y^(A1) in thegeneral formula (2).

Furthermore, the substituent represented by R³ of Y^(H1) on the nitrogenatom may be connected to X^(H5) or X^(H12) to form a ring.

In the general formula (9), X^(H1) to X^(H15) each independentlyrepresent CR⁴ or N, and CR⁴s each independently represent a hydrogenatom or a substituent. The preferred ranges of X^(H1) to X^(H15) are thesame as the preferred ranges of X^(A1) to X^(A15) in the general formula(2).

The preferred relationship between Y^(H1) and X^(H1) to X^(H15) in thegeneral formula (9) is the same as the preferred relationship betweenY^(A1) and X^(A1) to X^(A15) in the general formula (2), that is, theposition of CR⁴ in the case where X^(H12) to X^(H15) have CR⁴ as asubstituent is preferably a position adjacent to Y^(H1) (the position ofX^(H12) in the general formula (9)).

The general formula (9) is more preferably represented by the generalformula (17) as described later.

In the present invention, the compound represented by the generalformula (1) is preferably a compound represented by any one of thegeneral formulae (2), (4) to (7), and (8) cut of the general formulae(2) to (9) from the viewpoints that the planarity and the stability ofmolecules are good, and the T₁ can be easily increased that a lightemitting material as described later, and more preferably a compoundrepresented by any one of the general formulae (2), (4) to (6), and (8)from the viewpoints that the T₁ can be easily increased that a lightemitting material as described later.

In the present invention, the compound represented by the generalformula (1) is preferably a compound represented by any one of thefollowing general formulae (10) to (17).

In the general formulae (10) to (17), Y^(A1) to Y^(H1) eachindependently represent CR¹R², NR³, O, S, or Se, and R¹ to R³ eachindependently represent a substituent. R^(A1) to R^(A15), R^(B1) toR^(B15), R^(C1) to R^(C15), R^(D1) to R^(D15), R^(E1) to R^(E15), R^(F1)to R^(F15), R^(G1) to R^(G15) and R^(H1) to R^(H15) each independentlyrepresent a hydrogen atom or a substituent.

In the general formula (10), the definition and the preferred range ofY^(A1) are the same as the definition and the preferred range of Y^(A1)in the general formula (2).

Furthermore, the substituent represented by R³ of Y^(A1) on the nitrogenatom may be connected to R^(A15) to form a ring.

In the general formula (10), R^(A1) to R^(A15) each independentlyrepresent a hydrogen atom or a substituent, and the preferred ranges ofR^(A1) to R^(A15) are the same as the preferred ranges of R⁴ containedin each of X^(A1) to X^(A15) in the case where X^(A1) to X^(A15) in thegeneral formula (2) represent all CR⁴.

The preferred relationship between Y^(A1) and R^(A1) to R^(A15) in thegeneral formula (10) is the same as the preferred relationship betweenY^(A1) in the general formula (2) and R⁴ contained in each of X^(A1) toX^(A15) in the case where X^(A1) to X^(A15) in the general formula (2)represent all CR⁴, that is, the position of the substituent in the casewhere R^(A12) to R^(A15) have a substituent is preferably a positionadjacent to Y^(A1) (the position of R^(A15) in the general formula(10)).

In the general formula (11), the definition and the preferred range ofY^(B1) are the same as the definition and the preferred range of Y^(B1)in the general formula (3).

Furthermore, the substituent represented by R³ of Y^(B1) on the nitrogenatom may be connected to R^(B1) or R^(B12) to form a ring.

In the general formula (11), R^(B1) to R^(B15) each independentlyrepresent a hydrogen atom or a substituent, and the preferred ranges ofR^(B1) to R^(B15) are the same as the preferred ranges of R⁴ containedin each of X^(B1) to X^(B15) in the case where X^(B1) to X^(B15) in thegeneral formula (3) represent all CR⁴.

The preferred relationship between Y^(B1) and R^(B1) to R^(B15) in thegeneral formula (11) is the same as the preferred relationship betweenY^(B1) in the general formula (3) and R⁴ contained in each of X^(B1) toX^(B15) in the case where X^(B1) to X^(B15) in the general formula (3)represent all CR⁴, that is, the position of the substituent in the casewhere R^(B12) to R^(B15) have a substituent is preferably a positionadjacent to Y^(B1) (the position of R^(B12) in the general formula(11)).

In the general formula (12), the definition and the preferred range ofY^(C1) are the same as the definition and the preferred range of Y^(C1)in the general formula (4).

Furthermore, the substituent represented by R³ of Y^(C1) on the nitrogenatom may be connected to R^(C6) or R^(C15) to form a ring.

In the general formula (12), R^(C1) to R^(C15) each independentlyrepresent a hydrogen atom or a substituent, and the preferred ranges ofR^(C1) to R^(C15) are the same as the preferred ranges of R⁴ containedin each of X^(C1) to X^(C15) in the case where X^(C1) to X^(C15) in thegeneral formula (4) represent all CR⁴.

The preferred relationship between Y^(C1) and R^(C1) to R^(C15) in thegeneral formula (12) is the same as the preferred relationship betweenY^(C1) in the general formula (4) and R⁴ contained in each of X^(C1) toX^(C15) in the case where X^(C1) to X^(C15) in the general formula (4)represent all CR⁴, that is, the position of the substituent in the casewhere R^(C12) to R^(C15) have a substituent is preferably a positionadjacent to Y^(C1) (the position of R^(C15) in the general formula(12)).

In the general formula (13), the definition and the preferred range ofY^(D1) are the same as the definition and the preferred range of Y^(D1)in the general formula (5).

Furthermore, the substituent represented by R³ of Y^(D1) on the nitrogenatom may be connected to R^(D12) to form a ring.

In the general formula (13), R^(D1) to R^(D15) each independentlyrepresent a hydrogen atom or a substituent, and the preferred ranges ofR^(D1) to R^(D15) are the same as the preferred ranges of R⁴ containedin each of X^(D1) to X^(D15) in the case where X^(D1) to X^(D15) in thegeneral formula (5) represent all CR⁴.

The preferred relationship between Y^(D1) and R^(D1) to R^(D15) in thegeneral formula (13) is the same as the preferred relationship betweenY^(D1) in the general formula (5) and R⁴ contained in each of X^(D1) toX^(D15) in the case where X^(D1) to X^(D15) in the general formula (5)represent all CR⁴, that is, the position of the substituent in the casewhere R^(D12) to R^(D15) have a substituent is preferably a positionadjacent to Y^(D1) (the position of R^(D12) in the general formula(13)).

In the general formula (14), the definition and the preferred range ofY^(E1) are the same as the definition and the preferred range of Y^(E1)in the general formula (6).

Furthermore, the substituent represented by R³ of Y^(E1) on the nitrogenatom may be connected to R^(E7) or R^(E15) to form a ring.

In the general formula (14), R^(E1) to R^(E15) each independentlyrepresent a hydrogen atom or a substituent, and the preferred ranges ofR^(E1) to R^(E15) are the same as the preferred ranges of R⁴ containedin each of X^(E1) to X^(E15) in the case where X^(E1) to X^(E15) in thegeneral formula (6) represent all CR⁴.

The preferred relationship between Y^(E1) and R^(E1) to R^(E15) in thegeneral formula (14) is the same as the preferred relationship betweenY^(E1) in the general formula (6) and R⁴ contained in each of X^(E1) toX^(E15) in the case where X^(E1) to X^(E15) in the general formula (6)represent all CR⁴, that is, the position of the substituent in the casewhere R^(E12) to R^(E15) have a substituent is preferably a positionadjacent to Y^(E1) (the position of R^(E15) in the general formula(14)).

In the general formula (15), the definition and the preferred range ofY^(F1) are the same as the definition and the preferred range of Y^(F1)in the general formula (7).

Furthermore, the substituent represented by R³ of Y^(F1) on the nitrogenatom may be connected to R^(F4) or R^(E12) to form a ring.

In the general formula (15), R^(F1) to R^(F15) each independentlyrepresent a hydrogen atom or a substituent, and the preferred ranges ofR^(F1) to R^(F15) are the same as the preferred ranges of R⁴ containedin each of X^(F1) to X^(F15) in the case where X^(F1) to X^(F15) in thegeneral formula (7) represent all CR⁴.

The preferred relationship between Y^(F1) and R^(F1) to R^(F15) in thegeneral formula (15) is the same as the preferred relationship betweenY^(F1) in the general formula (7) and R⁴ contained in each of X^(F5) toX^(F15) in the case where X^(F1) to X^(F15) in the general formula (7)represent all CR⁴, that is, the position of the substituent in the casewhere R^(F12) to R^(F15) have a substituent is preferably a positionadjacent to Y^(F1) (the position of R^(F12) in the general formula(15)).

In the general formula (16), the definition and the preferred range ofY^(G1) are the same as the definition and the preferred range of Y^(G1)in the general formula (8).

Furthermore, the substituent represented by R³ of Y^(G1) on the nitrogenatom may be connected to X^(G15) to form a ring.

In the general formula (16), R^(G1) to R^(G15) each independentlyrepresent a hydrogen atom or a substituent, and the preferred ranges ofR^(G1) to R^(G15) are the same as the preferred ranges of R⁴ containedin each of X^(G1) to X^(G15) in the case where X^(G1) to X^(G15) in thegeneral formula (8) represent all CR⁴.

The preferred relationship between Y^(G1) and R^(G1) to R^(G15) in thegeneral formula (16) is the same as the preferred relationship betweenY^(G1) in the general formula (8) and R⁴ contained in each of X^(G1) toX^(G15) in the case where X^(G1) to X^(G15) in the general formula (8)represent all CR⁴, that is, the position of the substituent in the casewhere R^(G12) to R^(G15) have a substituent is preferably a positionadjacent to Y^(G1) (the position of R^(G15) in the general formula(16)).

In the general formula (17), the definition and the preferred range ofY^(H1) are the same as the definition and the preferred range of Y^(H1)in the general formula (9).

Furthermore, the substituent represented by R³ of Y^(H1) on the nitrogenatom may be connected to R^(H5) or R^(H12) to form a ring.

In the general formula (17), R^(H1) to R^(H15) each independentlyrepresent a hydrogen atom or a substituent, and the preferred ranges ofR^(H1) to R^(H15) are the same as the preferred ranges of R⁴ containedin each of X^(H1) to X^(H15) in the case where X^(H1) to X^(H15) in thegeneral formula (9) represent all CR⁴.

The preferred relationship between Y^(H1) and R^(H1) to R^(H15) in thegeneral formula (17) is the same as the preferred relationship betweenY^(H1) in the general formula (9) and R⁴ contained in each of X^(H1) toX^(H15) in the case where X^(H1) to X^(H15) in the general formula (9)represent all CR⁴, that is, the position of the substituent in the casewhere R^(H12) to R^(H15) have a substituent is preferably a positionadjacent to Y^(H1) (the position of R^(H12) in the general formula(17)).

In the present invention, the compound represented by the generalformula (1) is preferably a compound represented by any one of thegeneral formulae (10), (12) to (15), and (16) out of the generalformulae (10) to (17) from the viewpoints that the planarity and thestability of molecules are good, and the T₁ can be easily increased thata light emitting material as described later, and more preferably acompound represented by any one of the general formulae (10), (12) to(14), and (16) from the viewpoints that the T₁ can be easily increasedthat a light emitting material as described later.

The molecular weight of the compound represented by the general formula(1) is usually from 400 to 1500, preferably from 450 to 1200, morepreferably from 500 to 1100, and still more preferably from 550 to 1000.The molecular weight of 450 or more is advantageous in forming anamorphous thin film of good quality, and the molecular weight of 1200 orless is advantageous in improving solubility and sublimation properties,and thus improving the purity of the compound. In the organicelectroluminescent element of the present invention, the molecularweight of the compound represented by the general formula (1) ispreferably 550 or more from the viewpoint of a glass transitiontemperature. On the other hand, from the viewpoint of lamination of acomposition including the compound represented by the general formula(1) by deposition, the molecular weight of the compound represented bythe general formula (1) is preferably 1200 or less.

In the case where the hydrocarbon compound represented by the generalformula (1) is used in a host material of a light emitting layer or in acharge transporting material of a layer adjacent to the light emittinglayer, in an organic electroluminescent element, when the energy gap inthe thin film state (the minimum excited triplet (T₁) energy in the thinfilm state in the case of the light emitting material being aphosphorescence emitting material) is larger than in the light emissionmaterial as described later, the quench of the light emission isprevented, which is advantageous in enhancing the efficiency. On theother hand, from the viewpoint of chemical stability of the compound, itis preferable that an energy gap and T₁ energy be not too large.

In the present invention, the value of LUMO of the compound representedby the general formula (1), as determined by an electron densityfunctional theory (B3LYP/6-31G (d) level), is preferably more than 1.25,more preferably 1.4 or more, and particularly preferably from 1.4 to1.9.

The minimum excited triplet (T₁) energy in the film state of thecompound represented by the general formula (1) is preferably from 1.77eV (40 kcal/mol) to 3.51 eV (81 kcal/mol), and more preferably from 2.39eV (55 kcal/mol) to 3.25 eV (75 kcal/mol). In the organicelectroluminescent element of the present invention, it is preferablethat T₁ energy of the compound represented by the general formula (1) bemore than T₁ energy of the above-mentioned phosphorescent light emittingmaterial, from the viewpoint of luminous efficiency. In particular whenthe luminescent color from the organic electroluminescent element isgreen (the light emission peak wavelength is from 490 nm to 580 nm),from the viewpoint of luminous efficiency, T₁ energy is more preferablyfrom 2.39 eV (55 kcal/mol) to 2.82 eV (65 kcal/mol).

By measuring the phosphorescent light emitting spectrum of a thin filmof the material, the T₁ energy can be found from the short-wavelengthend thereof. For instance, a film of the material is formed in athickness of about 50 nm by a vacuum deposition method over a washedquartz glass substrate, and the phosphorescence spectrum of the thinfilm is measured using an F-7000 Hitachi spectrofluoro-photometer(Hitachi High-Technologies Corporation) at the temperature of liquidnitrogen. The T₁ energy can be found by converting the rising wavelengthon the short-wavelength side of the light emission spectrum thusobtained to energy units.

From the viewpoint of stable operation of the organic electroluminescentelement with respect to heat emission during high-temperature driving orelement driving, the glass transition temperature of the compoundrepresented by the general formula (1) in the organic electroluminescentelement of the present invention is preferably a compound having a glasstransition temperature of 100° C. or higher. The glass transitiontemperature (Tg) of the compound represented by the general formula (1)is more preferably from 100° C. to 400° C., particularly preferably from120° C. to 400° C., and still more preferably from 140° C. to 400° C.

If the purity of the compound represented by the general formula (1) islow, impurities serve as a trap for charge transport or acceleratedegradation of the element, and therefore, higher purity of the compoundrepresented by the general formula (1) is preferred. The purity can bemeasured, for example, by high performance liquid chromatography (HPLC),and the surface area ratio of the compound represented by the generalformula (1) as detected at an optical absorption intensity of 254 nm ispreferably 95.0% or more, and more preferably 97.0% or more,particularly preferably 99.0% or more, and most preferably 99.9% ormore. Examples of a method for increasing the purity of the compoundrepresented by the general formula (1) include recrystallization andsublimation.

Specific examples of the compound represented by the general formula (1)are list, but the present invention is not limited thereto.

In the compounds represented by the following general formula (10),R^(A1), R^(A4), R^(A6) to R^(A9), R^(A11) to R^(A14) represent ahydrogen atom, and the other groups are groups described in Tablesbelow.

TABLE 1 Com- pound No. Y^(A1) R^(A15) R^(A10) R^(A5) R³ R¹ R² O-10-1  OH H H — — — O-10-2  O H

— — — O-10-3  O H

H — — — O-10-4  O H

— — — O-10-5  O

— — — O-10-6  O H

H — — — O-10-7  O H H

— — — O-10-8  O H

— — — O-10-9  O H

— — — O-10-10 O H

H — — — O-10-11 O H

— — — O-10-12 O

H H — — — O-10-13 O H

— — — O-10-14 O H

H — — — O-10-15 O H

— — —

TABLE 2 O-10-16 O H

H — — — O-10-17 O H

— — — O-10-18 O H

H — — — O-10-19 O H

— — — O-10-20 O H

H — — — O-10-21 O H

— — — O-10-22 O H

H — — — O-10-23 O H

H — — — O-10-24 O H

— — — O-10-25 O H

H — — — O-10-26 O H

— — — S-10-1 S H H H — — — S-10-2 S H

— — — S-10-3 S H

H — — — S-10-4 S H

— — —

TABLE 3 S-10-5  S

— — — S-10-6  S H

H — — — S-10-7  S H H

— — — S-10-8  S H

— — — S-10-9  S H

— — — S-10-10 S H

H — — — S-10-11 S H

— — — S-10-12 S

H H — — — S-10-13 S H

— — — S-10-14 S H

H — — — S-10-15 S H

— — — S-10-16 S H

H — — — S-10-17 S H

— — — S-10-18 S H

H — — — S-10-19 S H

— — —

TABLE 4 S-10-20 S H

H — — — S-10-21 S H

— — — S-10-22 S H

H — — — S-10-23 S H

H — — — S-10-24 S H

— — — S-10-25 S H

H — — — S-10-26 S H

— — — N-10-1 NR³ H H H

— — N-10-2 NR³ H

— — N-10-3 NR³ H

H

— — N-10-4 NR³ H

— — N-10-5 NR³ H

H

— — N-10-6 NR³ H H

— — N-10-7 NR³ H

— — N-10-8 NR³ H

— —

TABLE 5 N-10-9  NR³ H

H

— — N-10-10 NR³ H

— — N-10-11 NR³ H

— — N-10-12 NR³ H

H

— — N-10-13 NR³ H

— — N-10-14 NR³ H

H

— — N-10-15 NR³ H

— — N-10-16 NR³ H

H

— — N-10-17 NR³ H

— — N-10-18 NR³ H

H

— — N-10-19 NR³ H

— — N-10-20 NR³ H

H

— — N-10-21 NR³ H

H

— — N-10-22 NR³ H

— — N-10-23 NR³ H

H

— —

TABLE 6 N-10- 24 NR³ H

— — C-10- CR¹R² H H H — *—Me *—Me 1  C-10- 2  CR¹R² H

— *—Me *—Me C-10- 3  CR¹R² H

H — *—Me *—Me C-10- 4  CR¹R² H

— *—Me *—Me C-10- 5  CR¹R² H

H —

C-10- 6  CR¹R² H H

— *—Me *—Me C-10- 7  CR¹R² H

—

C-10- 8  CR¹R² H

— *—Me *—Me C-10- 9  CR¹R² H

H —

C-10- 10 CR¹R² H

— *—Me *—Me C-10- 11 CR¹R² H

— *—Me *—Me C-10- 12 CR¹R² H

H — *—Me *—Me C-10- 13 CR¹R² H

— *—Me *—Me C-10- 14 CR¹R² H

H — *—Me *—Me

TABLE 7 C-10-15 CR¹R² H

— *—Me *—Me C-10-16 CR¹R² H

H —

C-10-17 CR¹R² H

— *—Me *—Me C-10-18 CR¹R² H

H — *—Me *—Me C-10-19 CR¹R² H

— *—Me *—Me C-10-20 CR¹R² H

H — *—Me *—Me C-10-21 CR¹R² H

— *—Me *—Me C-10-22 CR¹R² H

— *—Me *—Me C-10-23 CR¹R² H

H —

C-10-24 CR¹R² H

— *—Me *—Me

TABLE 8 Compound No. Central skeleton Substituent O-10-27

O-10-28

O-10-29

O-10-30

O-10-31

O-10-32

O-10-33

O-10-34

O-10-35

O-10-36

O-10-37

O-10-38

O-10-39

O-10-40

O-10-41

O-10-42

O-10-43

O-10-44

O-10-45

O-10-46

O-10-47

O-10-48

O-10-49

O-10-50

O-10-51

O-10-52

O-10-53

O-10-54

O-10-55

O-10-56

O-10-57

O-10-58

O-10-59

O-10-60

O-10-61

O-10-62

O-10-63

O-10-64

O-10-65

In the compounds represented by the following general formula (11),R^(B1), R^(B4), R^(B6) to R^(B9), R^(B11), R^(B13) to R^(B15) eachrepresent a hydrogen atom, and the other groups are the groups describedin Tables below.

TABLE 9 Compound No. Y^(B1) R^(B12) R^(B10) R^(B5) R³ R¹ R² O-11-1 O H HH — — — O-11-2 O H

— — — O-11-3 O H

H — — — O-11-4 O H

— — — O-11-5 O

— — — O-11-6 O H

H — — — O-11-7 O H H

— — — O-11-8 O H

— — — O-11-9 O H

— — — O-11-10 O H

H — — — O-11-11 O H

— — — O-11-12 O H

— — — O-11-13 O

H H — — — O-11-14 O H

H — — — O-11-15 O H

— — —

TABLE 10 O-11-16 O H

H — — — O-11-17 O H

— — — O-11-18 O H

H — — — O-11-19 O H

— — — O-11-20 O H

H — — — O-11-21 O H

— — — O-11-22 O H

H — — — O-11-23 O H

— — — O-11-24 O H

H — — — O-11-25 O H

— — — O-11-26 O H

H — — — O-11-27 O H

— — — S-11-1 S H H H — — — S-11-2 S H

— — — S-11-3 S H

H — — —

TABLE 11 S-11-4 S H

— — — S-11-5 S

— — — S-11-6 S H

H — — — S-11-7 S H H

— — — S-11-8 S H

— — — S-11-9 S H

— — — S-11-10 S H

H — — — S-11-11 S H

— — — S-11-12 S H

— — — S-11-13 S

H H — — — S-11-14 S H

H — — — S-11-15 S H

— — — S-11-16 S H

H — — — S-11-17 S H

— — — S-11-18 S H

H — — —

TABLE 12 S-11-19 S H

— — — S-11-20 S H

H — — — S-11-21 S H

— — — S-11-22 S H

H — — — S-11-23 S H

— — — S-11-24 S H

H — — — S-11-25 S H

— — — S-11-26 S H

H — — — S-11-27 S H

— — — N-11-1 NR³ H H H

— — N-11-2 NR³ H

— — N-11-3 NR³ H

H

— — N-11-4 NR³ H

— — N-11-5 NR³ H

H

— — N-11-6 NR³ H H

— —

TABLE 13 N-11-7 NR³ H

— — N-11-8 NR³ H

— — N-11-9 NR³ H

H

— — N-11-10 NR³ H

— — N-11-11 NR³ H

— — N-11-12 NR³ H

H

— — N-11-13 NR³ H

— — N-11-14 NR³ H

H

— — N-11-15 NR³ H

— — N-11-16 NR³ H

H

— — N-11-17 NR³ H

— — N-11-18 NR³ H

H

— — N-11-19 NR³ H

— — N-11-20 NR³ H

H

— — N-11-21 NR³ H

— —

TABLE 14 N-11-22 NR³ H

H

— — N-11-23 NR³ H

— — N-11-24 NR³ H

H

— — N-11-25 NR³ H

— — C-11-1 CR¹R² H H H — *—Me *—Me C-11-2 CR¹R² H

— *—Me *—Me C-11-3 CR¹R² H

H — *—Me *—Me C-11-4 CR¹R² H

— *—Me *—Me C-11-5 CR¹R² H

H —

C-11-6 CR¹R² H H

— *—Me *—Me C-11-7 CR¹R² H

—

C-11-8 CR¹R² H

— *—Me *—Me C-11-9 CR¹R² H

H —

C-11-10 CR¹R² H

— *—Me *—Me C-11-11 CR¹R² H

— *—Me *—Me

TABLE 15 C-11-12 CR¹R² H

H — *—Me *—Me C-11-13 CR¹R² H

— *—Me *—Me C-11-14 CR¹R² H

H — *—Me *—Me C-11-15 CR¹R² H

— *—Me *—Me C-11-16 CR¹R² H

H —

C-11-17 CR¹R² H

— *—Me *—Me C-11-18 CR¹R² H

H — *—Me *—Me C-11-19 CR¹R² H

— *—Me *—Me C-11-20 CR¹R² H

H — *—Me *—Me C-11-21 CR¹R² H

— *—Me *—Me C-11-22 CR¹R² H

H — *—Me *—Me C-11-23 CR¹R² H

—

C-11-24 CR¹R² H

H — *—Me *—Me C-11-25 CR¹R² H

— *—Me *—Me

In the compounds represented by the following general formula (12),R^(C1), R^(C3), R^(C6) to R^(C9), R^(C11) to R^(C14) each represent ahydrogen atom, and the other groups are the groups described in Tablesbelow.

TABLE 16 Compound No Y^(C1) R^(C15) R^(C10) R^(C2) R³ R¹ R² O-12-1 O H HH — — — O-12-2 O H

— — — O-12-3 O H

H — — — O-12-4 O H

— — — O-12-5 O

— — — O-12-6 O H

H — — — O-12-7 O H H

— — — O-12-8 O H

— — — O-12-9 O H

— — — O-12-10 O H

H — — — O-12-11 O H

— — — O-12-12 O H

— — — O-12-13 O

H H — — — O-12-14 O H

H — — — O-12-15 O H

— — —

TABLE 17 O-12-16 O H

H — — — O-12-17 O H

— — — O-12-18 O H

H — — — O-12-19 O H

— — — O-12-20 O H

H — — — O-12-21 O H

— — — O-12-22 O H

H — — — O-12-23 O H

— — — O-12-24 O H

H — — — O-12-25 O H

— — — O-12-26 O H

H — — — O-12-27 O H

— — — S-12-1 S H H H — — — S-12-2 S H

— — — S-12-3 S H

H — — —

TABLE 18 S-12-4 S H

— — — S-12-5 S

— — — S-12-6 S H

H — — — S-12-7 S H H

— — — S-12-8 S H

— — — S-12-9 S H

— — — S-12-10 S H

H — — — S-12-11 S H

— — — S-12-12 S H

— — — S-12-13 S

H H — — — S-12-14 S H

H — — — S-12-15 S H

— — — S-12-16 S H

H — — — S-12-17 S H

— — — S-12-18 S H

H — — —

TABLE 19 S-12-19 S H

— — — S-12-20 S H

H — — — S-12-21 S H

— — — S-12-22 S H

H — — — S-12-23 S H

— — — S-12-24 S H

H — — — S-12-25 S H

— — — S-12-26 S H

H — — — S-12-27 S H

— — — N-12-1 NR³ H H H

— — N-12-2 NR³ H

— — N-12-3 NR³ H

H

— — N-12-4 NR³ H

— — N-12-5 NR³ H

H

— — N-12-6 NR³ H H

— —

TABLE 20 N-12-7 NR³ H

— — N-12-8 NR³ H

— — N-12-9 NR³ H

H

— — N-12-10 NR³ H

— — N-12-11 NR³ H

— — N-12-12 NR³ H

H

— — N-12-13 NR³ H

— — N-12-14 NR³ H

H

— — N-12-15 NR³ H

— — N-12-16 NR³ H

H

— — N-12-17 NR³ H

— — N-12-18 NR³ H

H

— — N-12-19 NR³ H

— — N-12-20 NR³ H

H

— — N-12-21 NR³ H

— —

TABLE 21 N-12-22 NR³ H

H

— — N-12-23 NR³ H

— — N-12-24 NR³ H

H

— — N-12-25 NR³ H

— — C-12-1 CR¹R² H H H — *—Me *—Me C-12-2 CR¹R² H

— *—Me *—Me C-12-3 CR¹R² H

H — *—Me *—Me C-12-4 CR¹R² H

— *—Me *—Me C-12-5 CR¹R² H

H —

C-12-6 CR¹R² H H

— *—Me *—Me C-12-7 CR¹R² H

—

C-12-8 CR¹R² H

— *—Me *—Me C-12-9 CR¹R² H

H —

C-12-10 CR¹R² H

— *—Me *—Me C-12-11 CR¹R² H

— *—Me *—Me

TABLE 22 C-12-12 CR¹R² H

H — *—Me *—Me C-12-13 CR¹R² H

— *—Me *—Me C-12-14 CR¹R² H

H — *—Me *—Me C-12-15 CR¹R² H

— *—Me *—Me C-12-16 CR¹R² H

H —

C-12-17 CR¹R² H

— *—Me *—Me C-12-18 CR¹R² H

H — *—Me *—Me C-12-19 CR¹R² H

— *—Me *—Me C-12-20 CR¹R² H

H — *—Me *—Me C-12-21 CR¹R² H

— *—Me *—Me C-12-22 CR¹R² H

H — *—Me *—Me C-12-23 CR¹R² H

—

C-12-24 CR¹R² H

H — *—Me *—Me C-12-25 CR¹R² H

— *—Me *—Me

TABLE 23 Compound No. Central Skeleton Substituent O-12-28

O-12-29

O-12-30

O-12-31

O-12-32

O-12-33

O-12-34

O-12-35

O-12-36

O-12-37

O-12-38

O-12-39

O-12-40

O-12-41

O-12-42

O-12-43

O-12-44

O-12-45

O-12-46

O-12-47

O-12-48

O-12-49

O-12-50

O-12-51

O-12-52

O-12-53

O-12-54

O-12-55

O-12-56

O-12-57

O-12-58

O-12-59

O-12-60

O-12-61

O-12-62

O-12-63

O-12-64

O-12-65

O-12-66

In the compound represented by the following general formula (13),R^(D1), R^(D3), R^(D6) to R^(D9), R^(D11), R^(D13) to R^(D15) eachrepresent a hydrogen atom, and the other groups are the groups describedin Tables below.

TABLE 24 Compound No. Y^(D1) R^(D12) R^(D10) R^(D2) R³ R¹ R² O-13-1 O HH H — — — O-13-2 O H

— — — O-13-3 O H

H — — — O-13-4 O H

— — — O-13-5 O

H — — — O-13-6 O H

H — — — O-13-7 O H H

— — — O-13-8 O H

— — — O-13-9 O H

— — — O-13-10 O H

H — — — O-13-11 O H

— — — O-13-12 O H

— — — O-13-13 O

H H — — — O-13-14 O H

H — — — O-13-15 O H

— — —

TABLE 25 O-13-16 O H

H — — — O-13-17 O H

— — — O-13-18 O H

H — — — O-13-19 O H

— — — O-13-20 O H

H — — — O-13-21 O H

— — — O-13-22 O H

H — — — O-13-23 O H

— — — O-13-24 O H

H — — — O-13-25 O H

— — — O-13-26 O H

H — — — O-13-27 O H

— — — S-13-1 S H H H — — — S-13-2 S H

— — — S-13-3 S H

H — — —

TABLE 26 S-13-4 S H

— — — S-13-5 S

H — — — S-13-6 S H

H — — — S-13-7 S H H

— — — S-13-8 S H

— — — S-13-9 S H

— — — S-13-10 S H

H — — — S-13-11 S H

— — — S-13-12 S H

— — — S-13-13 S

H H — — — S-13-14 S H

H — — — S-13-15 S H

— — — S-13-16 S H

H — — — S-13-17 S H

— — — S-13-18 S H

H — — —

TABLE 27 S-13-19 S H

— — — S-13-20 S H

H — — — S-13-21 S H

— — — S-13-22 S H

H — — — S-13-23 S H

— — — S-13-24 S H

H — — — S-13-25 S H

— — — S-13-26 S H

H — — — S-13-27 S H

— — — N-13-1 NR³ H H H

— — N-13-2 NR³ H

— — N-13-3 NR³ H

H

— — N-13-4 NR³ H

— — N-13-5 NR³ H

H

— — N-13-6 NR³ H H

— —

TABLE 28 N-13-7 NR³ H

— — N-13-8 NR³ H

— — N-13-9 NR³ H

H

— — N-13-10 NR³ H

— — N-13-11 NR³ H

— — N-13-12 NR³ H

H

— — N-13-13 NR³ H

— — N-13-14 NR³ H

H

— — N-13-15 NR³ H

— — N-13-16 NR³ H

H

— — N-13-17 NR³ H

— — N-13-18 NR³ H

H

— — N-13-19 NR³ H

— — N-13-20 NR³ H

H

— — N-13-21 NR³ H

— —

TABLE 29 N-13-22 NR³ H

H

— — N-13-23 NR³ H

— — N-13-24 NR³ H

H

— — N-13-25 NR³ H

— — C-13-1 CR¹R² H H H — *—Me *—Me C-13-2 CR¹R² H

— *—Me *—Me C-13-3 CR¹R² H

H — *—Me *—Me C-13-4 CR¹R² H

— *—Me *—Me C-13-5 CR¹R² H

H —

C-13-6 CR¹R² H H

— *—Me *—Me C-13-7 CR¹R² H

—

C-13-8 CR¹R² H

— *—Me *—Me C-13-9 CR¹R² H

H —

C-13-10 CR¹R² H

— *—Me *—Me C-13-11 CR¹R² H

— *—Me *—Me

TABLE 30 C-13-12 CR¹R² H

H — *—Me *—Me C-13-13 CR¹R² H

— *—Me *—Me C-13-14 CR¹R² H

H — *—Me *—Me C-13-15 CR¹R² H

— *—Me *—Me C-13-16 CR¹R² H

H —

C-13-17 CR¹R² H

— *—Me *—Me C-13-18 CR¹R² H

H — *—Me *—Me C-13-19 CR¹R² H

— *—Me *—Me C-13-20 CR¹R² H

H — *—Me *—Me C-13-21 CR¹R² H

— *—Me *—Me C-13-22 CR¹R² H

H — *—Me *—Me C-13-23 CR¹R² H

—

C-13-24 CR¹R² H

H — *—Me *—Me C-13-25 CR¹R² H

— *—Me *—Me

TABLE 31 Compound No. Central Skeleton Substituent O-13-28

O-13-29

O-13-30

O-13-31

O-13-32

O-13-33

O-13-34

O-13-35

O-13-36

O-13-37

O-13-38

O-13-39

O-13-40

O-13-41

O-13-42

O-13-43

O-13-44

O-13-45

O-13-46

O-13-47

O-13-48

O-13-49

O-13-50

O-13-51

O-13-52

O-13-53

O-13-54

O-13-55

O-13-56

O-13-57

O-13-58

O-13-59

O-13-60

O-13-61

O-13-62

O-13-63

O-13-64

O-13-65

O-13-66

In the compound represented by the following general formula (14),R^(E1), R^(E3), R^(E4), R^(E7) to R^(E9), R^(E11), R^(E13) to R^(E15)each represent a hydrogen atom, and the other groups are the groupsdescribed in Tables below.

TABLE 32 Compound No. Y^(E1) R^(E15) R^(E10) R^(E2) R³ R¹ R² O-14-1 O HH H — — — O-14-2 O H

— — — O-14-3 O H

H — — — O-14-4 O H

— — — O-14-5 O

H H — — — O-14-6 O H

H — — — O-14-7 O H H

— — — O-14-8 O H

— — — O-14-9 O H

— — — O-14-10 O H

H — — — O-14-11 O H

— — — O-14-12 O H

— — — O-14-13 O

H — — — O-14-14 O H

H — — — O-14-15 O H

— — —

TABLE 33 O-14-16 O H

H — — — O-14-17 O H

— — — O-14-18 O H

H — — — O-14-19 O H

— — — O-14-20 O H

H — — — O-14-21 O H

— — — O-14-22 O H

H — — — O-14-23 O H

— — — O-14-24 O H

H — — — O-14-25 O H

— — — O-14-26 O H

H — — — O-14-27 O H

— — — S-14-1 S H H H — — — S-14-2 S H

— — — S-14-3 S H

H — — —

TABLE 34 S-14-4 S H

— — — S-14-5 S

H H — — — S-14-6 S H

H — — — S-14-7 S H H

— — — S-14-8 S H

— — — S-14-9 S H

— — — S-14-10 S H

H — — — S-14-11 S H

— — — S-14-12 S H

— — — S-14-13 S

H — — — S-14-14 S H

H — — — S-14-15 S H

— — — S-14-16 S H

H — — — S-14-17 S H

— — — S-14-18 S H

H — — —

TABLE 35 S-14-19 S H

— — — S-14-20 S H

H — — — S-14-21 S H

— — — S-14-22 S H

H — — — S-14-23 S H

— — — S-14-24 S H

H — — — S-14-25 S H

— — — S-14-26 S H

H — — — S-14-27 S H

— — — N-14-1 NR³ H H H

— — N-14-2 NR³ H

— — N-14-3 NR³ H

H

— — N-14-4 NR³ H

— — N-14-5 NR³ H

H

— — N-14-6 NR³ H H

— —

TABLE 36 N-14-7  NR³ H

— — N-14-8  NR³ H

— — N-14-9  NR³ H

H

— — N-14-10 NR³ H

— — N-14-11 NR³ H

— — N-14-12 NR³ H

H

— — N-14-13 NR³ H

— — N-14-14 NR³ H

H

— — N-14-15 NR³ H

— — N-14-16 NR³ H

H

— — N-14-17 NR³ H

— — N-14-18 NR³ H

H

— — N-14-19 NR³ H

— — N-14-20 NR³ H

H

— — N-14-21 NR³ H

— —

TABLE 37 N-14- 22 NR³ H

H

— — N-14- 23 NR³ H

— — N-14- 24 NR³ H

H

— — N-14- 25 NR³ H

— — C-14- 1 CR¹R² H H H — *—Me *—Me C-14- 2 CR¹R² H

— *—Me *—Me C-14- 3 CR¹R² H

H — *—Me *—Me C-14- 4 CR¹R² H

— *—Me *—Me C-14- 5 CR¹R² H

H —

C-14- 6 CR¹R² H H

— *—Me *—Me C-14- 7 CR¹R² H

—

C-14- 8 CR¹R² H

— *—Me *—Me C-14- 9 CR¹R² H

H —

C-14- 10 CR¹R² H

— *—Me *—Me C-14- 11 CR¹R² H

— *—Me *—Me

TABLE 38 C-14-12 CR¹R² H

H — *—Me *—Me C-14-13 CR¹R² H

— *—Me *—Me C-14-14 CR¹R² H

H — *—Me *—Me C-14-15 CR¹R² H

— *—Me *—Me C-14-16 CR¹R² H

H —

C-14-17 CR¹R² H

— *—Me *—Me C-14-18 CR¹R² H

H — *—Me *—Me C-14-19 CR¹R² H

— *—Me *—Me C-14-20 CR¹R² H

H — *—Me *—Me C-14-21 CR¹R² H

— *—Me *—Me C-14-22 CR¹R² H

H — *—Me *—Me C-14-23 CR¹R² H

—

C-14-24 CR¹R² H

H — *—Me *—Me C-14-25 CR¹R² H

— *—Me *—Me

TABLE 39 Compound No. Central Skeleton Substituent O-14-28

O-14-29

O-14-30

O-14-31

O-14-32

O-14-33

O-14-34

O-14-35

O-14-36

O-14-37

O-14-38

O-14-39

O-14-40

O-14-41

O-14-42

O-14-43

O-14-44

O-14-45

O-14-46

O-14-47

O-14-48

O-14-49

O-14-50

O-14-51

O-14-52

O-14-53

TABLE 40 Compound No. Central Skeleton Substituent O-14-54

O-14-55

O-14-56

O-14-57

O-14-58

O-14-59

O-14-60

O-14-61

O-14-62

O-14-63

O-14-64

O-14-65

O-14-66

O-14-67

O-14-68

O-14-69

O-14-70

O-14-71

O-14-72

O-14-73

O-14-74

O-14-75

O-14-76

O-14-77

O-14-78

O-14-79

TABLE 41 Compound No. Central Skeleton Substituent N-14-26

N-14-27

N-14-28

N-14-29

N-14-30

N-14-31

N-14-32

N-14-33

N-14-34

N-14-35

N-14-36

N-14-37

N-14-38

N-14-39

N-14-40

N-14-41

N-14-42

N-14-43

N-14-44

N-14-45

N-14-46

N-14-47

N-14-48

N-14-49

N-14-50

N-14-51

N-14-52

N-14-53

N-14-54

N-14-55

TABLE 42 Compound No. Central Skeleton Substituent N-14-56

N-14-57

N-14-58

N-14-59

N-14-60

N-14-61

N-14-62

N-14-63

N-14-64

N-14-65

N-14-66

N-14-67

N-14-68

N-14-69

N-14-70

N-14-71

N-14-72

N-14-73

N-14-74

N-14-75

N-14-76

N-14-77

N-14-78

N-14-79

N-14-80

N-14-81

N-14-82

N-14-83

N-14-84

N-14-85

N-14-86

N-14-87

N-14-88

N-14-89

N-14-90

N-14-91

N-14-92

N-14-93

N-14-94

In the compound represented by the following general formula (15),R^(F1), R^(F3), R^(F4), R^(F7) to R^(F9), R^(F11), R^(F13) to R^(F15)each represent a hydrogen atom, and the other groups are the groupsdescribed in Tables below.

TABLE 43 Compound No. Y^(F1) R^(F12) R^(F10) R^(F2) R³ R¹ R² O-15-1 O HH H — — — O-15-2 O H

— — — O-15-3 O H

H — — — O-15-4 O H

— — — O-15-5 O

H — — — O-15-6 O H

H — — — O-15-7 O H H

— — —

TABLE 44 O-15-16 O H

H — — — O-15-17 O H

— — — O-15-18 O H

H — — — O-15-19 O H

— — — O-15-20 O H

H — — — O-15-21 O H

— — — O-15-22 O H

H — — — O-15-23 O H

— — — O-15-24 O H

H — — — O-15-25 O H

— — — O-15-26 O H

H — — — O-15-27 O H

— — — S-15-1  S H H H — — — S-15-2  S H

— — — S-15-3  S H

H — — —

TABLE 45 S-15-4  S H

— — — S-15-5  S

H — — — S-15-6  S H

H — — — S-15-7  S H H

— — — S-15-8  S H

— — — S-15-9  S H

— — — S-15-10 S H

H — — — S-15-11 S H

— — — S-15-12 S H

— — — S-15-13 S

H H — — — S-15-14 S H

H — — — S-15-15 S H

— — — S-15-16 S H

H — — — S-15-17 S H

— — — S-15-18 S H

H — — —

TABLE 46 S-15-19 S H

— — — S-15-20 S H

H — — — S-15-21 S H

— — — S-15-22 S H

H — — — S-15-23 S H

— — — S-15-24 S H

H — — — S-15-25 S H

— — — S-15-26 S H

H — — — S-15-27 S H

— — — N-15-1  NR³ H H H

— — N-15-2  NR³ H

— — N-15-3  NR³ H

H

— — N-15-4  NR³ H

— — N-15-5  NR³ H

H

— — N-15-6  NR³ H H

— —

TABLE 47 N-15-7  NR³ H

— — N-15-8  NR³ H

— — N-15-9  NR³ H

H

— — N-15-10 NR³ H

— — N-15-11 NR³ H

— — N-15-12 NR³ H

H

— — N-15-13 NR³ H

— — N-15-14 NR³ H

H

— — N-15-15 NR³ H

— — N-15-16 NR³ H

H

— — N-15-17 NR³ H

— — N-15-18 NR³ H

H

— — N-15-19 NR³ H

— — N-15-20 NR³ H

H

— — N-15-21 NR³ H

— —

TABLE 48 N-15- 22 NR³ H

H

— — N-15- 23 NR³ H

— — N-15- 24 NR³ H

H

— — N-15- 25 NR³ H

— — C-15- 1 CR¹R² H H H — *—Me *—Me C-15- 2 CR¹R² H

C-15- 3 CR¹R² H

H — *—Me *—Me C-15- 4 CR¹R² H

— *—Me *—Me C-15- 5 CR¹R² H

H —

C-15- 6 CR¹R² H H

— *—Me *—Me C-15- 7 CR¹R² H

—

C-15- 8 CR¹R² H

— *—Me *—Me C-15- 9 CR¹R² H

H —

C-15- 10 CR¹R² H

— *—Me *—Me C-15- 11 CR¹R² H

— *—Me *—Me

TABLE 49 C-15-12 CR¹R² H

H — *—Me *—Me C-15-13 CR¹R² H

— *—Me *—Me C-15-14 CR¹R² H

H — *—Me *—Me C-15-15 CR¹R² H

— *—Me *—Me C-15-16 CR¹R² H

H —

C-15-17 CR¹R² H

— *—Me *—Me C-15-18 CR¹R² H

H — *—Me *—Me C-15-19 CR¹R² H

— *—Me *—Me C-15-20 CR¹R² H

H — *—Me *—Me C-15-21 CR¹R² H

— *—Me *—Me C-15-22 CR¹R² H

H — *—Me *—Me C-15-23 CR¹R² H

—

C-15-24 CR¹R² H

H — *—Me *—Me C-15-25 CR¹R² H

— *—Me *—Me

In the following general formula (16), R^(G1), R^(G3), R^(G4), R^(G5),R^(G8), R^(G9), R^(G11), and R^(G11), and R^(G12) to R^(G14) eachrepresent a hydrogen atom, and the other groups are the groups describedin Tables below.

TABLE 50 Com- pound No. Y^(G1) R^(G15) R^(G10) R^(G2) R³ R¹ R² O-16-1  OH H H — — — O-16-2  O H

— — — O-16-3  O O H

— — — O-16-4  O H

— — — O-16-5  O

H — — — O-16-7  O H H

— — — O-16-8  O H

— — — O-16-9  O H

— — — O-16-10 O H

H — — — O-16-11 O H

— — — O-16-12 O H

— — — O-16-13 O

H H — — — O-16-14 O H

H — — — O-16-15 O H

— — —

TABLE 51 O-16-16 O H

H — — — O-16-17 O H

— — — O-16-18 O H

H — — — O-16-19 O H

— — — O-16-20 O H

H — — — O-16-21 O H

— — — O-16-22 O H

H — — — O-16-23 O H

— — — O-16-24 O H

H — — — O-16-25 O H

— — — O-16-26 O H

H — — — O-16-27 O H

— — — S-16-1 S H H H — — — S-16-2 S H

— — — S-16-3 S H

H — — —

TABLE 52 S-16-4 S H

— — — S-16-5 S

H — — — S-16-6 S H

H — — — S-16-7 S H H

— — — S-16-8 S H

— — — S-16-9 S H

— — — S-16-10 S H

H — — — S-16-11 S H

— — — S-16-12 S H

— — — S-16-13 S

H H — — — S-16-14 S H

H — — — S-16-15 S H

— — — S-16-16 S H

H — — — S-16-17 S H

— — — S-16-18 S H

H — — —

TABLE 53 S-16-19 S H

— — — S-16-20 S H

H — — — S-16-21 S H

— — — S-16-22 S H

H — — — S-16-23 S H

— — — S-16-24 S H

H — — — S-16-25 S H

— — — S-16-26 S H

H — — — S-16-27 S H

— — — N-16-1 NR³ H H H

— — N-16-2 NR³ H

— — N-16-3 NR³ H

H

— — N-16-4 NR³ H

— — N-16-5 NR³ H

H

— — N-16-6 NR³ H H

— —

TABLE 54 N-16-7 NR³ H

— — N-16-8 NR³ H

— — N-16-9 NR³ H

H

— — N-16-10 NR³ H

— — N-16-11 NR³ H

— — N-16-12 NR³ H

H

— — N-16-13 NR³ H

— — N-16-14 NR³ H

H

— — N-16-15 NR³ H

— — N-16-16 NR³ H

H

— — N-16-17 NR³ H

— — N-16-18 NR³ H

H

— — N-16-19 NR³ H

— — N-16-20 NR³ H

H

— — N-16- 21 NR³ H

— —

TABLE 55 N-16-22 NR³ H

H

— — N-16-23 NR³ H

— — N-16-24 NR³ H

H

— — N-16-25 NR³ H

— — C-16-1 CR¹R² H H H — *—Me *—Me C-16-2 CR¹R² H

— *—Me *—Me C-16-3 CR¹R² H

H — *—Me *—Me C-16-4 CR¹R² H

— *—Me *—Me C-16-5 CR¹R² H

H —

C-16-6 CR¹R² H H

— *—Me *—Me C-16-7 CR¹R² H

—

C-16-8 CR¹R² H

— *—Me *—Me C-16-9 CR¹R² H

H —

C-16-10 CR¹R² H

— *—Me *—Me C-16-11 CR¹R² H

— *—Me *—Me

TABLE 56 C-16-12 CR¹R² H

H — *—Me *—Me C-16-13 CR¹R² H

— *—Me *—Me C-16-14 CR¹R² H

H — *—Me *—Me C-16-15 CR¹R² H

— *—Me *—Me C-16-16 CR¹R² H

H —

C-16-17 CR¹R² H

— *—Me *—Me C-16-18 CR¹R² H

H — *—Me *—Me C-16-19 CR¹R² H

— *—Me *—Me C-16-20 CR¹R² H

H — *—Me *—Me C-16-21 CR¹R² H

— *—Me *—Me C-16-22 CR¹R² H

H — *—Me *—Me C-16-23 CR¹R² H

—

C-16-24 CR¹R² H

H — *—Me *—Me C-16-25 CR¹R² H

— *—Me *—Me

TABLE 57 Compound No. Central Skeleton Substituent O-16-28

O-16-29

O-16-30

O-16-31

O-16-32

O-16-33

O-16-34

O-16-35

O-16-36

O-16-37

O-16-38

O-16-39

O-16-40

O-16-41

O-16-42

O-16-43

O-16-44

O-16-45

O-16-46

O-16-47

O-16-48

O-16-49

O-16-50

O-16-51

O-16-52

O-16-53

TABLE 58 Compound No. Compound Skeleton Substituent O-16-54

O-16-55

O-16-56

O-16-57

O-16-58

O-16-59

O-16-60

O-16-61

O-16-62

O-16-63

O-16-64

O-16-65

O-16-66

O-16-67

O-16-68

O-16-69

O-16-70

O-16-71

O-16-72

O-16-73

O-16-74

O-16-75

O-16-76

O-16-77

O-16-78

O-16-79

In the compound represented by following general formula (17), R^(H1),R^(H3), R^(H4), R^(H8), R^(H9), R^(H11), to R^(H15) each represent ahydrogen atom, and the other groups are the groups described in Tablesbelow.

TABLE 59 Compound No. Y^(H1) R^(H12) R^(H2) R^(H10) R³ R¹ R² O-17-2 O H

— — — O-17-3 O H

H — — — O-17-4 O H

— — — O-17-5 O

H H — — — O-17-6 O H

— — — O-17-7 O H H

— — — O-17-8 O H

— — — O-17-9 O H

— — — O-17-10 O H

H — — — O-17-11 O H

— — — O-17-12 O H

— — — O-17-13 O

H — — — O-17-14 O H

H — — — O-17-15 O H

— — — O-17-16 O H

H — — —

TABLE 60 O-17-17 O H

— — — O-17-18 O H

H — — — O-17-19 O H

— — — O-17-20 O H

H — — — O-17-21 O H

— — — O-17-22 O H

H — — — O-17-23 O H

— — — O-17-24 O H

H — — — O-17-25 O H

— — — O-17-26 O H

H — — — O-17-27 O H

— — — S-17-1 S H H H — — — S-17-2 S H

— — — S-17-3 S H

H — — — S-17-4 S H

— — —

TABLE 61 S-17-5

  S

H H — — — S-17-6 S H

H — — — S-17-7 S H H

— — — S-17-8 S H

— — — S-17-9 S H

— — — S-17-10 S H

H — — — S-17-11

  S H

— — — S-17-12 S H

— — — S-17-13 S

H — — — S-17-14 S H

H — — — S-17-15 S H

— — — S-17-16 S H

H — — — S-17-17 S H

— — — S-17-18 S H

H — — — S-17-19 S H

  — — —

TABLE 62 S-17-20 S H

H — — — S-17-21 S H

— — — S-17-22 S H

H — — — S-17-23 S H

— — — S-17-24 S H

H — — — S-17-25 S H

— — — S-17-26 S H

  H — — — S-17-27 S H

— — — N-17-1 NR³ H H H

— — N-17-2 NR³ H

— — N-17-3 NR³ H

H

— — N-17-4 NR³ H

— — N-17-5 NR³ H

H

  — — N-17-6 NR³ H H

— — N-17-7 NR³ H

— —

TABLE 63 N-17-8 NR³ H

— — N-17-9 NR³ H

H

— — N-17-10 NR³ H

— — N-17-11 NR³ H

— — N-17-12 NR³ H

H

— — N-17-13 NR³ H

— — N-17-14 NR³ H

H

— — N-17-15 NR³ H

— — N-17-16 NR³ H

H

— — N-17-17 NR³ H

— — N-17-18 NR³ H

H

— — N-17-19 NR³ H

— — N-17-20 NR³ H

H

— — N-17-21 NR³ H

— — N-17-22 NR³ H

H

— —

TABLE 64 N-17-23 NR³ H

— — N-17-24 NR³ H

H

— — N-17-25 NR³ H

— — C-17-1 CR¹R² H H H — *—Me *—Me C-17-2 CR¹R² H

— *—Me *—Me C-17-3 CR¹R² H

H — *—Me *—Me C-17-4 CR¹R² H

— *—Me *—Me C-17-5 CR¹R² H

H —

C-17-6 CR¹R² H H

— *—Me *—Me C-17-7 CR¹R² H

—

C-17-8 CR¹R² H

— *—Me *—Me C-17-9 CR¹R² H

H —

C-17-10 CR¹R² H

— *—Me *—Me C-17-11 CR¹R² H

— *—Me *—Me C-17-12 CR¹R² H

H — *—Me *—Me

TABLE 65 C-17-13 CR¹R² H

— *—Me *—Me C-17-14 CR¹R² H

H — *—Me *—Me C-17-15 CR¹R² H

— *—Me *—Me C-17-16 CR¹R² H

H —

C-17-17 CR¹R² H

— *—Me *—Me C-17-18 CR¹R² H

H — *—Me *—Me C-17-19 CR¹R² H

— *—Me *—Me C-17-20 CR¹R² H

H — *—Me *—Me C-17-21 CR¹R² H

— *—Me *—Me C-17-22 CR¹R² H

H — *—Me *—Me C-17-23 CR¹R² H

—

C-17-24 CR¹R² H

H — *—Me *—Me C-17-25 CR¹R² H

— *—Me *—Me

The compounds exemplified as the compound represented by the generalformula (1) can be synthesized by the methods described in, for example,WO2010/042107, WO2010/131855, JP-21-2010-087496, and the like.

The compounds represented by the general formulae (2) to (9) can be eachpreferably synthesized by the following scheme. However, the followingsynthesis scheme is one of synthesis and the synthesis can be alsoconducted by other known methods.

Synthesis Route of General Formula (2)

In the present invention, the compound represented by the generalformula (1) is not limited in its use and can be contained in any one ofthe organic layers. With regard to the layer into which the compoundrepresented by the general formula (1) is introduced, the compound ispreferably contained in any one of the light emitting layer, a layerbetween the light emitting layer and the cathode (in particular, a layeradjacent to the light emitting layer), and a layer between the lightemitting layer and the anode, more preferably contained in any one ofthe light emitting layer, an electron transporting layer, an electroninjecting layer, an exciton blocking layer, a hole blocking layer, andan electron blocking layer, or in a plurality of layers thereof, stillmore preferably contained in any one of the light emitting layer, anelectron transporting layer, a hole blocking layer, and a holetransporting layer, and particularly preferably contained in the lightemitting layer or an electron transporting layer. Further, the compoundrepresented by the general formula (1) may be used in a plurality of thelayers. For example, the compound may be used in both of the lightemitting layer and an electron transporting layer.

In the case where the compound represented by the general formula (1) iscontained in the light emitting layer, the compound represented by thegeneral formula (1) is contained in the amount of, preferably 0.1% bymass to 99% by mass, more preferably 1% by mass to 97% by mass, andstill more preferably 10% by mass to 96% by mass, with respect to thetotal mass of the light emitting layer. In the case where the compoundrepresented by the general formula (1) is further contained in thelayers other than the light emitting layer, it is contained in theamount of, preferably 50% by mass to 100% by mass, and more preferably85% by mass to 100% by mass, with respect to the total mass of thelayers other than the light emitting layer.

(Phosphorescent Light Emitting Material)

In the present invention, the light emitting layer preferably containsat least one phosphorescent light emitting material. In the presentinvention, in addition to the phosphorescent light emitting material, afluorescent light emitting material or a phosphorescent light emittingmaterial other than the phosphorescent light emitting material containedin the light emitting layer can be used as the light emitting material.

The fluorescent light emitting material and the phosphorescent lightemitting material are described in detail in, for example, paragraphNos. [0100] to [0164] of JP-A-2008-270736 and paragraph Nos. [0088] to[0090] of JP-A-2007-266458, and the detailed descriptions in thesepublications can be applied to the present invention.

Examples of the phosphorescent light emitting material which can be usedin the present invention include phosphorescent light emitting compoundsdescribed in patent documents, for example, U.S. Pat. No. 6,303,238B1,U.S. Pat. No. 6,097,147, WO00/57676, WO00/70655, WO01/08230,WO01/39234A2, WO01/41512A1, WO002/02714A2, WO02/15645A1, WO02/44189A1,WO05/19373A2, JP-A-2001-247859, JP-A-2002-302671, JP-A-2002-117978,JP-A-2003-133074, JP-A-2002-235076, JP-A-2003-123982, JP-A-2002-170684,EP1211257, JP-A-2002-226495, JP-A-2002-234894, JP-A-2001-247859,JP-A-2001-298470, JP-A-2002-173674, JP-A-2002-203678, JP-A-2002-203679,JP-A-2004-357791, JP-A-2006-256999, JP-A-2007-19462, JP-A-2007-84635,and JP-A-2007-96259. Above all, examples of the light emitting materialwhich is more preferred include phosphorescent light emitting metalcomplex compounds such as Ir complexes, Pt complexes, Cu complexes, Recomplexes, W complexes, Rh complexes, Ru complexes, Pd complexes, Oscomplexes, Eu complexes, Tb complexes, Gd complexes, Dy complexes, andCe complexes, with Ir complexes, Pt complexes, and Re complexes beingparticularly preferred. Above all, Ir complexes, Pt complexes, and Recomplexes each including at least one coordination mode of ametal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, and ametal-sulfur bond are preferred. Furthermore, from the viewpoints ofluminous efficiency, driving durability, and chromaticity, Ir complexesand Pt complexes are particularly preferred, and Ir complexes are themost preferred.

These phosphorescent light emitting metal complex compounds arepreferably contained together with the compound represented by thegeneral formula (1) in the light emitting layer.

As the phosphorescent light emitting material contained in the lightemitting layer, an iridium complex represented by the general formula(E-1) shown below is preferably used. The iridium complex represented bythe general formula (E-1) will be described below.

In the general formula (E-1), Z¹ and Z² each independently represent acarbon atom or a nitrogen atom.

A¹ represents an atomic group that together with Z¹ and a nitrogen atomforms a 5- or 6-membered hetero ring.

B¹ represents an atomic group that together with Z² and a carbon atomforms a 5- or 6-membered ring.

(X—Y) represents a mono-anionic bidentate ligand.

n_(E1) represents an integer of 1 to 3.

n_(E1) represents an integer of 1 to 3, and preferably 2 or 3.

Z¹ and Z² each independently represent a carbon atom or a nitrogen atom.Z¹ and Z² are each preferably a carbon atom.

A¹ represents an atomic group that together with Z¹ and a nitrogen atomforms a 5- or 6-membered hetero ring. Examples of the 5- of 6-memberedhetero ring formed of A¹, Z¹, and a nitrogen atom include a pyridinering, a pyrimidine ring, a pyrazine ring, a triazine ring, an imidazolering, a pyrazole ring, an oxazole ring, a thiazole ring, a triazolering, an oxadiazole ring, and a thiadiazole ring.

From the viewpoints of stability of complexes, control of light emittingwavelength, and luminescent quantum yield, examples of the 5- of6-membered hetero ring formed of A¹, Z¹, and a nitrogen atom preferablyinclude a pyridine ring, a pyrazine ring, an imidazole ring, and apyrazole ring, more preferably include a pyridine ring, an imidazolering, and a pyrazine ring, still more preferably include a pyridine ringand an imidazole ring, and most preferably include a pyridine ring.

The 5- of 6-membered hetero ring formed of A¹, Z¹, and a nitrogen atommay have a substituent, and as the substituent, the Substituent Group Acan be applied. The substituent is appropriately selected to control thelight emitting wavelength and the potentials, but in the case ofshortening the wavelength, an electron donating group, a fluorine atom,and an aromatic ring group are preferred, and for example, an alkylgroup, a dialkylamino group, an alkoxy group, a fluorine atom, an arylgroup, a heteroaryl group, and the like are selected. Further, in thecase of increasing the wavelength, an electron withdrawing group ispreferred, and for example, a cyano group, a perfluoroalkyl group, andthe like are preferably selected. For the purpose of adjusting themolecular interaction, an alkyl group, a cycloalkyl group, an arylgroup, and the like are preferably selected.

The substituent on carbon is preferably an alkyl group, a perfluoroalkylgroup, an aryl group, a heteroaryl group, a dialkylamino group, adiarylamino group, an alkoxy group, a cyano group, or a fluorine atom.

The substituent on nitrogen is preferably an alkyl group, an aryl group,or a heteroaryl group, and from the viewpoint of the stability ofcomplexes, the substituent is preferably an alkyl group or an arylgroup.

The substituents may be connected to each other to form a fused ring,and examples of the ring thus formed include a benzene ring, a pyridinering, a pyrazine ring, a pyridazine ring, a pyrimidine ring, animidazole ring, an oxazole ring, a thiazole ring, a pyrazole ring, athiophene ring, and a furan ring. The ring thus formed may have asubstituent, and examples of the substituent include the substituents oncarbon atoms and the substituents on nitrogen atoms, as described above.

B¹ represents a 5- or 6-membered ring containing Z² and carbon atoms.Examples of the 5- or 6-membered ring formed of B¹, Z² and a carbon atominclude a benzene ring, a pyridine ring, a pyrimidine ring, a pyrazinering, a pyridazine ring, a triazine ring, an imidazole ring, a pyrazolering, an oxazole ring, a thiazole ring, a triazole ring, an oxadiazolering, a thiadiazole ring, a thiophene ring, and a furan ring.

From the viewpoints of the stability of complexes, the control of lightemitting wavelength, and the luminescent quantum yield, the 5- or6-membered ring formed of B¹, Z² and a carbon atom is preferably abenzene ring, a pyridine ring, a pyrazine ring, an imidazole ring, apyrazole ring, or a thiophene ring, more preferably a benzene ring, apyridine ring, or a pyrazole ring, and still more preferably a benzenering or a pyridine ring.

The 5- or 6-membered ring formed of B1, Z² and a carbon atom may have asubstituent, as the substituent on a carbon atom, the Substituent GroupA can be applied, and as the substituent on a nitrogen atom, theSubstituent Group B can be applied.

The substituent on carbon is preferably an alkyl group, a perfluoroalkylgroup, an aryl group, a heteroaryl group, a dialkylamino group, adiarylamino group, an alkoxy group, a cyano group, or a fluorine atom.

The substituent on carbon is appropriately selected to control the lightemitting wavelength and the potentials, but in the case of increasingthe wavelength, an electron donating group and an aromatic ring groupare preferred, and for example, an alkyl group, a dialkylamino group, analkoxy group, an aryl group, a heteroaryl group, and the like areselected. Further, in the case of shortening the wavelength, an electronwithdrawing group is preferred, and for example, a fluorine atom, cyanogroup, a perfluoroalkyl group, and the like are selected. For thepurpose of adjusting the molecular interaction, an alkyl group, acycloalkyl group, an aryl group, and the like are preferably selected.

The substituent on nitrogen is preferably an alkyl group, an aryl group,or an aromatic hetero ring group, and from the viewpoint of thestability of complexes, the substituent is preferably an alkyl group oran aryl group. The substituents may be connected to each other to form afused ring, and examples of the ring thus formed include a benzene ring,a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring,an imidazole ring, an oxazole ring, a thiazole ring, a pyrazole ring, athiophene ring, and a furan ring. The ring thus formed may have asubstituent, and examples of the substituent include the substituents oncarbon atoms and the substituents on nitrogen atoms, as described above.

In addition, the substituents of the 5- or 6-membered ring formed of A¹,Z¹, and a nitrogen atom and the 5- or 6-membered ring formed of B¹, Z²,and a carbon atom may be connected to each other to form a fused ring asdescribed above.

(X—Y) represents a mono-anionic bidentate ligand. Examples of themono-anionic bidentate ligand described in pp. 89 to 90 of WO02/15645,Lamansky et al.

The mono-anionic bidentate ligand represented by (X—Y) is preferably amono-anionic bidentate ligand represented by the following generalformula (L-1).

In the general formula (L-1), R^(L1) and R^(L2) each independentlyrepresent an alkyl group, an aryl group, or a heteroaryl group.

R^(L3) represents a hydrogen atom, an alkyl group, an aryl group, or aheteroaryl group.

The alkyl group represented by R^(L1) to R^(L3) may have a substituent,and may be saturated or unsaturated. In the case where the alkyl grouphave a substituent, examples of the substituent include the followingsubstituent Z′, preferred examples of the substituent Z′ include aphenyl group, a heteroaryl group, a fluorine atom, a silyl group, anamino group, a cyano group, or a group formed by a combination thereof,and more preferably a phenyl group, a fluorine atom, or a cyano group.The alkyl group represented by R^(L1) to R^(L3) is preferably an alkylgroup having 1 to 8 carbon atoms, and more preferably an alkyl grouphaving 1 to 5 carbon atoms.

<<Substituent Z′>>

The substituents Z′ represents an alkyl group (preferably having 1 to 10carbon atoms, more preferably having 1 to 6 carbon atoms, and still morepreferably having 1 to 4 carbon atoms, for example, methyl, ethyl,isopropyl, n-propyl, tert-butyl, isobutyl, n-butyl, neopentyl, n-pentyl,n-hexyl, cyclopropyl, cyclopentyl, and cyclohexyl), an alkenyl group(preferably having 2 to 8 carbon atoms, and more preferably having 2 to5 carbon atoms, for example, vinyl), an aryl group (preferably having 6to 30 carbon atoms, and more preferably having 6 to 20 carbon atoms, forexample, a phenyl group, a naphthyl group, an anthacenyl group, atetracenyl group, a pyrenyl group, a perylenyl group, a triphenylenylgroup, and a chrysenyl group), a heteroaryl group (preferably having 4to 30 carbon atoms, and more preferably having 4 to 20 carbon atoms, forexample, pyridine, pyrazine, pyrimidine, pyridazine, triazine,thiophene, furan, oxazole, thiazole, imidazole, pyrazole, triazole,oxadiazole, and thiadiazole), an alkoxy group (preferably having 1 to 8carbon atoms, and more preferably having 1 to 5 carbon atoms, forexample, a methoxy group, an ethoxy group, an n-propyloxy group, and aniso-propyloxy group), a phenoxy group, a halogen atom (preferably afluorine atom), a silyl group (preferably having 4 to 30 carbon atoms,and more preferably having 4 to 20 carbon atoms, for example, atrimethylsilyl group, a triethylsilyl group, and a triphenylsilylgroup), an amino group (preferably having 2 to 60 carbon atoms, and morepreferably having 2 to 40 carbon atoms, for example, a dimethylaminogroup, a diethylamino group, and a diphenylamino group), a cyano group,or a group formed by a combination thereof. A plurality of substituentsZ′ may be connected to each other to form an aryl ring. Examples of thearyl ring formed by a mutual combination of a plurality of substituentsZ's include a phenyl ring and a pyridine ring, with a phenyl group beingpreferred.

The aryl groups represented by R^(L1) to R^(L3) may be subjected to ringfusion and may have a substituent. In the case of having a substituent,examples of the substituent include the above-described substituents Z′,and the substituent Z′ is preferably an alkyl group or an aryl group,and more preferably an alkyl group. The aryl group represented by R^(L1)to R^(L3) is preferably an aryl group having 6 to 30 carbon atoms, andmore preferably an aryl group having 6 to 18 carbon atoms.

The heteroaryl groups represented by R^(L1) to R^(L3) may be subjectedto ring fusion and may have a substituent. In the case of having asubstituent, examples of the substituent include the above-describedsubstituents Z′, and the substituent Z′ is preferably an alkyl group oran aryl group, and more preferably an alkyl group. The heteroaryl grouprepresented by R^(L1) to R^(L3) is preferably a heteroaryl group having4 to 12 carbon atoms, and more preferably a heteroaryl group having 4 to10 carbon atoms.

R^(L1) and R^(L2) are preferably an alkyl group or an aryl group, morepreferably an alkyl group or a phenyl group, and particularly preferablyan alkyl group.

The alkyl group represented by R^(L1) and R^(L2) is preferably an alkylgroup having a total carbon number of 1 to 8, and more preferably analkyl group having a total carbon number of 1 to 5, and examples thereofinclude a methyl group, an ethyl group, an n-propyl group, an iso-propylgroup, an iso-butyl group, a t-butyl group, an n-butyl group, and acyclohexyl group, preferably a methyl group, an ethyl group, aniso-butyl group, and a t-butyl group, and particularly preferably amethyl group.

R^(L3) is preferably a hydrogen atom, an alkyl group, or aryl group,more preferably a hydrogen atom or alkyl group, and particularlypreferably a hydrogen atom.

A preferred embodiment of the iridium complex represented by the generalformula (E-1) is an iridium complex material represented by thefollowing general formula (E-2).

Next, the general formula (E-2) will be described.

In the general formula (E-2), A^(E1) to A^(E8) each independentlyrepresent a nitrogen atom or C—R^(E).

R^(E) represents a hydrogen atom or a substituent.

(X—Y) represents a mono-anionic bidentate ligand.

n_(E2) represents an integer of 1 to 3.

A^(E1) to A^(E8) each independently represent a nitrogen atom orC—R^(E). R^(E) represents a hydrogen atom or a substituent, and R^(E)smay be connected to each other to form a ring. Examples of the ring thusformed include the same rings as the fused rings exemplified in thegeneral formula (E-1) as described above. Examples of the substituentrepresented by R^(E) include those exemplified as the Substituent GroupA.

A^(E1) to A^(E4) are preferably C—R^(E), and in the case where A^(E1) toA^(E4) are C—R^(E), R^(E) of A^(E3) is preferably a hydrogen atom, analkyl group, an aryl group, an amino group, an alkoxy group, an aryloxygroup, a fluorine atom, or a cyano group, more preferably a hydrogenatom, an alkyl group, an amino group, an alkoxy group, an aryloxy group,or a fluorine atom, particularly preferably a hydrogen atom or fluorineatom, and R^(E) of A^(E1), A^(E2) and A^(E4) is preferably a hydrogenatom, an alkyl group, an aryl group, an amino group, an alkoxy group, anaryloxy group, a fluorine atom, or a cyano group, more preferably ahydrogen atom, an alkyl group, an amino group, an alkoxy group, anaryloxy group, or a fluorine atom, and particularly preferably ahydrogen atom.

A^(E5) to A^(E8) are preferably C—R^(E), in the case where A^(E5) toA^(E8) are C—R^(E), R^(E) is preferably a hydrogen atom, an alkyl group,a perfluoroalkyl group, an aryl group, an aromatic hetero ring group, adialkylamino group, a diarylamino group, an alkyloxy group, a cyanogroup, or a fluorine atom, more preferably a hydrogen atom, an alkylgroup, a perfluoroalkyl group, an aryl group, a dialkylamino group, acyano group, or a fluorine atom, and still more preferably a hydrogenatom, an alkyl group, a trifluoromethyl group, or a fluorine atom.Further, if possible, the substituents may be connected to each other toform a fused ring structure. In the case where the light emittingwavelength is shifted to a short wavelength side, A^(E6) is preferably anitrogen atom.

(X—Y) and n_(E2) have the same meanings as (X—Y) and n_(E1) in thegeneral formula (E-1), and the preferred ranges thereof are also thesame.

A more preferred embodiment of the compound represented by the generalformula (E-2) is a compound represented by the following general formula(E-3).

In the general formula (E-3), R^(T1), R^(T2), R^(T3), R^(T4), R^(T5),R^(T6) and R^(T7) each independently represent a hydrogen atom, an alkylgroup, a cycloalkyl group, an alkenyl group, an alkynyl group, —CN, aperfluoroalkyl group, a trifluorovinyl group, —CO₂R, —C(O)R, —NR₂, —NO₂,—OR, a halogen atom, an aryl group, or a heteroaryl group, and further,it may have a substituent Z. Rs each independently represent a hydrogenatom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynylgroup, a heteroalkyl group, an aryl group, or a heteroaryl group.

A represents CR′ or a nitrogen atom, R′ represents a hydrogen atom, analkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group,—CN, a perfluoroalkyl group, a trifluorovinyl group, —CO₂R, —C(O)R,—NR₂, —NO₂, —OR, a halogen atom, an aryl group, or a heteroaryl group,and further, it may have a substituent Z. Rs each independentlyrepresent a hydrogen atom, an alkyl group, a perhaloalkyl group, analkenyl group, an alkynyl group, a heteroalkyl group, an aryl group, ora heteroaryl group.

Any two of R^(T1) to R^(T7), and R′ may be bonded to each other to formfused 4- to 7-membered rings, the fused 4- to 7-membered rings arecycloalkyl, aryl, or heteroaryl, and the fused 4- to 7-membered ringsmay further have substituents Z. Above all, it is preferable that R^(T1)and R^(T7), or R^(T5) ad R^(T6) be subjected to ring fusion to form abenzene ring, and it is particularly preferable that R^(T5) and R^(T6)be subjected to ring fusion to form a benzene ring.

Zs each independently represent a halogen atom, —R″, —OR″, —N(R″)₂,—SR″, —C(O)R″, —C(O)OR″, —C(O)N(R″)₂, —CN, —NO₂, —SO₂, —SOR″, —SO₂R″, or—SO₃R″, and R″s each independently represent a hydrogen atom, an alkylgroup, a perhaloalkyl group, an alkenyl group, an alkynyl group, aheteroalkyl group, an aryl group, or a heteroaryl group.

(X—Y) represents a mono-anionic bidentate ligand, and n_(E) ³ representsan integer of 1 to 3.

The alkyl group may have a substituent, and may be saturated orunsaturated, and examples of the group that may be the substituentinclude the above-described substituents Zs. The alkyl group representedby R^(T1) to R^(T7), and R′ is preferably an alkyl group having a totalcarbon number of 1 to 8, and more preferably an alkyl group having atotal carbon number of 1 to 6, and examples thereof include a methylgroup, an ethyl group, an i-propyl group, a cyclohexyl group, and at-butyl group.

The cycloalkyl group may have a substituent, and may be saturated orunsaturated, and examples of the group that may be the substituteinclude the above-described substituent Z. The cycloalkyl grouprepresented by R^(T1) to R^(T7), and R′ is preferably a cycloalkyl grouphaving 4 to 7 ring members, more preferably a cycloalkyl group having atotal carbon number of 5 to 6, and examples thereof include acyclopenthyl group and a cyclohexyl group.

The alkenyl group represented by R^(T1) to R^(T7), and R′ preferably has2 to 30 carbon atoms, more preferably has 2 to 20 carbon atoms, andparticularly preferably has 2 to 10 carbon atoms, and examples thereofinclude vinyl, allyl, 1-propenyl, 1-isopropenyl, 1-butenyl, 2-butenyl,and 3-pentenyl.

The alkynyl group represented by R^(T1) to R^(T7), and R′ preferably has2 to 30 carbon atoms, more preferably has 2 to 20 carbon atoms, andparticularly preferably has 2 to 10 carbon atoms, and examples thereofinclude ethynyl, propargyl, 1-propynyl, and 3-pentynyl.

The perfluoroalkyl group represented by R^(T1) to R^(T7), and R′includes a group obtained by substituting all the hydrogen atoms in theabove-mentioned alkyl group with fluorine atoms.

The aryl group represented by R^(T1) to R^(T7), and R′ is preferably asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, andexamples thereof include a phenyl group, a tolyl group, and a naphthylgroup.

The heteroaryl group represented by R^(T1) to R^(T7), and R′ ispreferably a heteroaryl group having 5 to 8 carbon atoms, and morepreferably a substituted or unsubstituted 5- or 6-membered heteroarylgroup, and examples thereof include a pyridyl group, a pyrazinyl group,a pyridazinyl group, a pyrimidinyl group, a triazinyl group, aquinolinyl group, an isoquinolinyl group, a quinazolinyl group, acinnolinyl group, a phthalazinyl group, a quinoxalinyl group, a pyrrolylgroup, an indolyl group, a furyl group, a benzofuryl group, a thienylgroup, a benzothienyl group, a pyrazolyl group, an imidazolyl group, abenzimidazolyl group, a triazolyl group, an oxazolyl group, abenzoxazolyl group, a thiazolyl group, a benzothiazolyl group, anisothiazolyl group, a benzisothiazolyl group, a thiadiazolyl group, anisoxazolyl group, a benzisoxazolyl group, a pyrrolidinyl group, apiperidinyl group, a piperazinyl group, an imidazolidinyl group, athiazolinyl group, a sulfolanyl group, a carbazolyl group, adibenzofuryl group, a dibenzothienyl group, and a pyridoindolyl group.Preferred examples thereof are a pyridyl group, a pyrimidinyl group, animidazolyl group, and a thienyl group, and more preferred examples are apyridyl group and a pyrimidinyl group.

R^(T1) to R^(T7), and R′ are preferably a hydrogen atom, an alkyl group,a cyano group, a trifluoromethyl group, a perfluoroalkyl group, adialkylamino group, a fluoro group, an aryl group, or a heteroarylgroup, more preferably a hydrogen atom, an alkyl group, a cyano group, atrifluoromethyl group, a fluoro group, or an aryl group, and still morepreferably a hydrogen atom, an alkyl group, or an aryl group. Thesubstituent Z is preferably an alkyl group, an alkoxy group, a fluorogroup, a cyano group, or a dialkylamino group, and more preferably ahydrogen atom.

Any two of R^(T1) to R^(T7), and R′ may be bonded to each other to forma fused 4- to 7-membered ring, the fused 4- to 7-membered ring iscycloalkyl, aryl, or heteroaryl, and the fused 4- to 7-membered ring mayfurther have a substituent Z. The definitions and the preferred rangesof the formed cycloalkyl, aryl, and heteroaryl are the same as thecycloalkyl group, the aryl group, and the heteroaryl group defined inR^(T1) to R^(T7), and R′.

Further, a case where A represents CR′ and 0 to 2 members of R^(T1) toR^(T7), and R′ is/are an alkyl group or a phenyl group and theremainders are all hydrogen atoms is particularly preferred, and a casewhere 0 to 2 members of R^(T1) to R^(T7), and R′ is/are an alkyl groupand the remainders are all hydrogen atoms is particularly preferred.

n_(E3) is preferably 2 or 3. With regard to the kind of the ligands inthe complex, the ligands are preferably constituted of one or two kinds,and more preferably constituted of one kind. When a reactive group isintroduced to the complex molecule, the ligand preferably includes twokinds from the viewpoint of easy synthesis.

(X—Y) has the same definition as (X—Y) in the general formula (E-1) andthe preferred range thereof is also the same.

One of preferred embodiments of the compound represented by the generalformula (E-3) is a compound represented by the following general formula(E-4).

In the general formula (E-4), R^(T1) to R^(T4), A, (X—Y) and n_(E) ⁴have the same definitions as R^(T1) to R^(T4), A, (X—Y) and n_(E3) inthe general formula (E-3), and the preferred ranges thereof are also thesame. R¹′ to R⁵′ each independently represent a hydrogen atom, an alkylgroup, a cycloalkyl group, an alkenyl group, an alkynyl group, —CN, aperfluoroalkyl group, a trifluorovinyl group, —CO₂R, —C(O)R, —NR₂, —NO₂,—OR, a halogen atom, an aryl group, or a heteroaryl group. Further, theymay have a substituent Z. Rs each independently represent a hydrogenatom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynylgroup, a heteroalkyl group, an aryl group, or a heteroaryl group.

Any two of R¹′ to R⁵′ may be bonded to each other to form a fused 4- to7-membered ring, the fused 4- to 7-membered ring is cycloalkyl, aryl, orheteroaryl, and the fused 4- to 7-membered ring may further have asubstituent Z.

Zs each independently represent a halogen atom, —R″, —OR″, —N(R″)₂,—SR″, —C(O)R″, —C(O)OR″, —C(O)N(R″)₂, —CN, —NO₂, —SO₂, —SOR″, —SO₂R″, or—SO₃R″, and R″s each independently represent a hydrogen atom, an alkylgroup, a perhaloalkyl group, an alkenyl group, an alkynyl group, aheteroalkyl group, an aryl group, or a heteroaryl group.

In addition, the preferred ranges of R¹′ to R⁵′ are the same as those ofR^(T1) to R^(T7), and R′ in general formula (E-3). Further, a case whereA represents CR′ and, 0 to 2 members of R^(T1) to R^(T4), R′, and R¹′ toR⁵′ represent (s) an alkyl group or a phenyl group, and the remaindersare all hydrogen atoms is particularly preferred, and a case where 0 to2 members of R^(T1) to R^(T4), R′, and R¹′ to R⁵′ is/are alkyl groups,and the remainders are all hydrogen atoms is still more preferred.

Preferred specific examples of the compound represented by the generalformula (E-1) are listed below, but the compound is not limited thereto.

The compound exemplified as the compound represented by the generalformula (E-1) can be synthesized by various methods described inJP-A-2009-99783, U.S. Pat. No. 7,279,232, and the like. After thesynthesis, the compound is preferably purified by column chromatography,recrystallization, or the like, and then purified by sublimationpurification. By sublimation purification, it is possible not only toseparate organic impurities but also to effectively remove the inorganicsalts, remaining solvent, or the like.

Although the phosphorescent light emitting material is preferablycontained in the light emitting layer, the use thereof is not limited,and further, the phosphorescent light emitting material may also becontained in any further layer of the organic layers.

The phosphorescent light emitting material in the light emitting layeris preferably contained in the light emitting layer generally in anamount of 0.1% by mass to 50% by mass with respect to the total mass ofthe compounds forming the light emitting layer, and from the viewpointof durability and external quantum efficiency, the phosphorescent lightemitting material is more preferably contained in an amount of 1% bymass to 50% by mass, and particularly preferably contained in an amountof 2% by mass to 40% by mass.

(3) Other Host Materials

Host materials, which can be used in the light emitting layer, otherthan the compound represented by the general formula (1) include acompound having the following structure as a partial structure:

conductive high-molecular oligomers such as aromatic hydrocarbon,pyrrole, indole, carbazole, azaindole, indolocarbazole, azacarbazole,triazole, oxazole, oxadiazole, pyrazole, imidazole, thiophene,polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine,amino-substituted chalcone, styrylanthracene, hydrazone, stilbene,silazane, an aromatic tertiary amine compound, a styrylamine compound, aporphyrin-based compound, a polysilane-based compound, apoly(N-vinylcarbazole), an aniline-based copolymer, a thiopheneoligomer, and a polythiophene, organic silane, a carbon film, pyridine,pyrimidine, triazine, fluorenone, anthraquinodimethane, anthrone,diphenylquinone, thiopyran dioxide, carbodiimide, fluorenylidenemethane,distyrylpyrazine, a fluorine-substituted aromatic compound, heterocyclictetracarboxylic anhydride such as naphthalene perylene, phthalocyanine,and various metal complexes typified by metal complexes of 8-quinolinolderivatives and metal complexes having metal phthalocyanine,benzoxazole, or benzothiazole as a ligand thereof, and derivativesthereof (which may have a substituent or a fused ring), and the like.

(Other Layers)

The organic electroluminescent element of the present invention mayinclude layers other than the light emitting layer.

Examples of the organic layer other than the light emitting layer whichmay be included in the organic layer include a hole injecting layer, ahole transporting layer, a blocking layer (a hole blocking layer, anelectron blocking layer, an exciton blocking layer, and the like), andan electron transporting layer. Specific examples of the layerconfiguration include those described below, but the present inventionis not limited to these configurations.

-   -   Anode/Hole transporting layer/Light emitting layer/Electron        transporting layer/Cathode,    -   Anode/Hole transporting layer/Light emitting layer/Blocking        layer/Electron transporting layer/Cathode,    -   Anode/Hole transporting layer/Light emitting layer/Blocking        layer/Electron transporting layer/Electron injecting        layer/Cathode,    -   Anode/Hole injecting layer/Hole transporting layer/Light        emitting layer/Blocking layer/Electron transporting        layer/Cathode,    -   Anode/Hole injecting layer/Hole transporting layer/Light        emitting layer/Electron transporting layer/Electron injecting        layer/Cathode,    -   Anode/Hole injecting layer/Hole transporting layer/Light        emitting layer/Blocking layer/Electron transporting        layer/Electron injecting layer/Cathode,    -   Anode/Hole injecting layer/Hole transporting layer/Blocking        layer/Light emitting layer/Blocking layer/Electron transporting        layer/Electron injecting layer/Cathode.

The organic electroluminescent element of the present inventionpreferably includes at least one (A) organic layer which is preferablydisposed between the anode and the light emitting layer. Examples of the(A) organic layer which is preferably disposed between the anode and thelight emitting layer include an hole injecting layer, a holetransporting layer, and an electron blocking layer from the anode side.

The organic electroluminescent element of the present inventionpreferably includes at least one (B) organic layer which is preferablydisposed between the cathode and the light emitting layer. Examples ofthe (B) organic layer which is preferably disposed between the cathodeand the light emitting layer include an electron injecting layer, anelectron transporting layer, and a hole blocking layer from the cathodeside.

Specifically, an example of the preferred embodiments of the organicelectroluminescent element according to the present invention is theembodiment shown in FIG. 1, in which a hole injecting layer 4, a holetransporting layer 5, a light emitting layer 6, a hole blocking layer 7,and an electron transporting layer 8 are laminated as the organic layer,in this order from the anode 3 side.

Hereinafter, the layers other than the light emitting layer which theorganic electroluminescent element of the present invention may havewill be described.

(A) Organic Layer Preferably Disposed Between Anode and Light EmittingLayer

First, the (A) organic layer preferably disposed between the anode andthe light emitting layer will be described.

(A-1) Hole Injecting Layer and Hole Transporting Layer

The hole injecting layer and the hole transporting layer are layershaving a function of receiving holes from the anode or the anode sideand transporting them to the cathode side. The hole injecting materialand the hole transporting material used in these layers may be either alow molecular compound or a high molecular compound.

For the hole injecting layer and the hole transporting layer, thematters described in paragraph Nos. [0165] to [0167] of JP-A-2008-270736can be applied to the present invention.

The hole injecting layer preferably contains an electron receivingdopant. By incorporating the electron receiving dopant into the holeinjecting layer, for example, there are brought such effects that thehole injecting properties are enhanced, that the driving voltage islowered, and that the efficiency is enhanced. The electron receivingdopant may be any one of organic materials or inorganic materials solong as the material is capable of withdrawing electrons from thematerial to be doped and generating radical cations, and examplesthereof include a TCNQ compound such as tetracyanoquinodimethane (TCNQ)and tetrafluorotetracyanoquinodimethane (F₄-TCNQ), a hexaazatriphenylenecompound such as hexacyanohexaazatriphenylene (HAT-CN, a compound LG 101used in Examples as described later), and molybdenum oxide. Byinterposing only the electron receiving dopant above, as a thin film,between the anode and the hole transporting layer, the same effect canbe provided. In this case, this layer is referred to as a hole injectinglayer. In addition, also by interposing the electron receiving dopant,as a thin film, between hole transporting layers, the same effect can beprovided. In this case, one hole injecting layer or multiple holeinjecting layers may be interposed between the hole transporting layers.

The electron receiving dopant in the hole injecting layer is preferablycontained in an amount of 0.01% by mass to 50% by mass, more preferablyin an amount of 0.1% by mass to 40% by mass, and more preferably in anamount of 0.2% by mass to 30% by mass, with respect to the total mass ofthe compounds forming the hole injecting layer. In the case of beingused as a thin film, the thickness of the hole injecting layer ispreferably from 1 nm to 50 nm, more preferably from 3 nm to 30 nm, andstill more preferably from 5 nm to 20 nm.

(A-2) Electron Blocking Layer

The electron blocking layer is a layer having a function of preventingthe electrons, which have been transported from the cathode side to thelight emitting layer, from passing through to the anode side. In thepresent invention, the electron blocking layer can be provided as anorganic layer adjacent to the light emitting layer and the anode side.

As the organic compound constituting the electron blocking layer, forexample, those exemplified above as the hole transporting material canbe used.

The thickness of the electron blocking layer is preferably from 1 nm to500 nm, more preferably from 3 nm to 200 nm, and still more preferablyfrom 5 nm to 100 nm.

The electron blocking layer may have either a single layer structurecomposed of one kind or two or more kinds of materials selected from theabove-exemplified materials or a multilayer structure composed of aplurality of layers having the same composition or differentcompositions.

In order to inhibit energy transfer of excitons generated in the lightemitting layer to prevent degradation of luminous efficiency, T₁ energyin the film state of the organic compound constituting the electronblocking layer is preferably higher than the T₁ energy of the lightemitting material.

(A-3) Material Particularly Preferably Used in Organic Layer PreferablyDisposed Between Anode and Light Emitting Layer

[Compound Represented by General Formula (M-1)]

In the organic electroluminescent element of the present invention, as amaterial particularly preferably used in (A) the organic layerpreferably disposed between the anode and the light emitting layer, atleast one compound represented by the following general formula (M-1)may be exemplified.

The compound represented by the general formula (M-1) is preferablycontained in an organic layer that is located between the light emittinglayer and the anode and adjacent to the light emitting layer. The usethereof is however not limited and the compound may further be containedin any layer of the organic layers. The layer into which the compoundrepresented by the general formula (M-1) is introduced may be any one ofa light emitting layer, a hole injecting layer, a hole transportinglayer, an electron transporting layer, an electron injecting layer and acharge blocking layer, or the compound may be contained in a pluralityof layers thereof.

The organic layer that is located between the light emitting layer andthe anode and adjacent to the light emitting layer into which thecompound represented by the general formula (M-1) is contained is morepreferably an electron blocking layer or a hole transporting layer.

In the general formula (M-1), Ar¹ and Ar² each independently representalkyl, aryl, heteroaryl, arylamino, alkylamino, morpholino,thiomorpholino, a 5- or 6-membered heterocycloalkyl containing one ormore heteroatoms selected from N, O, and S, or a cycloalkyl, and mayfurther have a substituent Z. Ar¹ and Ar² may be bonded to each othervia a single bond, alkylene, or alkenylene (regardless of presence orabsence of a fused ring) to form a fused 5- to 9-membered ring.

Ar³ represents P-valent alkyl, aryl, heteroaryl or arylamino, and mayfurther have a substituent Z.

Zs each independently represent a halogen atom, —R″, —OR″, —N(R″)₂,—SR″, —C(O)R″, —C(O)OR″, —C(O)N(R″)₂, —CN, —NO₂, —SO₂, —SOR″, —SO₂R″, or—SO₃R″, and R″s each independently represent a hydrogen atom, an alkylgroup, a perhaloalkyl group, an alkenyl group, an alkynyl group, aheteroalkyl group, an aryl group, or a heteroaryl group.

p is an integer of 1 to 4, and when p is 2 or more, Ar¹s and Ar²s may bethe same as or different from each other, respectively.

Another preferred embodiment of the compound represented by the generalformula (M-1) is a case where the compound is represented by the generalformula (M-2).

In the general formula (M-2), R^(M1) represents an alkyl group, an arylgroup, or a heteroaryl group.

R^(M2) to R^(M23) each independently represent a hydrogen atom, an alkylgroup, an aryl group, a heteroaryl group, an alkoxy group, an aryloxygroup, an amino group, a silyl group, a cyano group, a nitro group, or afluorine atom.

In the general formula (M-2), R^(M1) represents an alkyl group(preferably having 1 to 8 carbon atoms), an aryl group (preferablyhaving 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4to 12 carbon atoms), and these groups may have the above-describedsubstituent Z. R^(M1) is preferably an aryl group or a heteroaryl group,and more preferably an aryl group. Examples of a preferred substituentin the case where the aryl group of R^(M1) has a substituent include analkyl group, a halogen atom, a cyano group, an aryl group and an alkoxygroup, more preferably an alkyl group, a halogen atom, a cyano group, oran aryl group, and still more preferably an alkyl group, a cyano group,or an aryl group. The aryl group of R^(M1) is preferably a phenyl groupwhich may have a substituent Z, and more preferably a phenyl group whichmay have an alkyl group or a cyano group.

R^(M2) to R^(M23) each independently represent a hydrogen atom, an alkylgroup (preferably having 1 to 8 carbon atoms), an aryl group (preferablyhaving 6 to 30 carbon atoms), a heteroaryl group (preferably having 4 to12 carbon atoms), an alkoxy group (preferably having 1 to 8 carbonatoms), an aryloxy group (preferably having 6 to 30 carbon atoms), anamino group (preferably having 0 to 24 carbon atoms), a silyl group(preferably having 0 to 18 carbon atoms), a cyano group, a nitro group,or a fluorine atom, and these groups may have the above-describedsubstituent Z.

R^(M2), R^(M7), R^(M8), R^(M15), R^(M16) and R^(M23) are each preferablya hydrogen atom, or an alkyl group or an aryl group which may have asubstituent Z, and more preferably a hydrogen atom.

R^(M4), R^(M5), R^(M11), R^(M12), R^(M19) and R^(M20) are eachpreferably a hydrogen atom, an alkyl group or an aryl group which mayhave a substituent Z, or a fluorine atom, and more preferably a hydrogenatom.

R^(M3), R^(M6), R^(M9), R^(M4), R^(M17), and R^(M22) are each preferablya hydrogen atom, an alkyl group or an aryl group which may have asubstituent Z, a fluorine atom, or a cyano group, more preferably ahydrogen atom or an alkyl group which may have a substituent Z, andstill more preferably a hydrogen atom.

R^(M10), R^(M13), R^(M18) and R^(M21) are each preferably a hydrogenatom, an alkyl group, an aryl group, a heteroaryl group, or an aminogroup which may have a substituent Z, a nitro group, a fluorine atom, ora cyano group, more preferably a hydrogen atom, an alkyl group, or anaryl group which may have a substituent Z, a nitro group, a fluorineatom, or a cyano group, and still more preferably a hydrogen atom or analkyl group which may have a substituent Z. As the substituent in thecase where the alkyl group has a substituent, a fluorine atom ispreferred, and the carbon number in the alkyl group that may have asubstituent Z is preferably from 1 to 6, and more preferably from 1 to4.

In another preferred embodiment, the compound represented by the generalformula (M-1) is represented by the following general formula (M-3).

In the general formula (M-3), R^(S1) to R^(S5) each independentlyrepresent an alkyl group, a cycloalkyl group, an alkenyl group, analkynyl group, —CN, a perfluoroalkyl group, a trifluorovinyl group,—CO₂R, —C(O)R, —NR₂, —NO₂, —OR, a halogen atom, an aryl group, or aheteroaryl group, and may further have a substituent Z. Rs eachindependently represent a hydrogen atom, an alkyl group, a perhaloalkylgroup, an alkenyl group, an alkynyl group, a heteroalkyl group, an arylgroup, or a heteroaryl group. When a plurality of R^(SL) to R^(S5)exist, those groups may be bonded to each other to form a ring, and mayfurther have a substituent Z.

a represents an integer of 0 to 4, and when a plurality of R^(S1)sexist, the R^(S1)s may be the same as or different from one another, andmay be bonded to each other to form a ring. b to e each independentlyrepresent an integer of 0 to 5, and when a plurality of groups exist foreach R^(S2) to R^(S5), the groups may be the same as or different fromone another, and any two thereof may be bonded to each other to form aring.

q is an integer of 1 to 5, and when q is 2 or more, a plurality ofR^(S1)s may be the same as or different from one another, and may bebonded to each other to form a ring.

The alkyl group may have a substituent, and may be saturated orunsaturated, and as the group that may be the substituent, theabove-described Z may be exemplified. The alkyl group represented byR^(S1) to R^(S5) is preferably an alkyl group having a total carbonnumber of 1 to 8, and more preferably an alkyl group having a totalcarbon number of 1 to 6, and examples thereof include a methyl group, anethyl group, an i-propyl group, a cyclohexyl group, and a t-butyl group.

The cycloalkyl group may have a substituent, and may be saturated orunsaturated, and as the group that may be the substitute, theabove-described substituent Z may be exemplified. The cycloalkyl grouprepresented by R^(S1) to R^(S5) is preferably a cycloalkyl group having4 to 7 ring members, and more preferably a cycloalkyl group having atotal carbon number of 5 to 6, and examples thereof include acyclopenthyl group and a cyclohexyl group.

The alkenyl group represented by R^(S1) to R^(S5) preferably has 2 to 30carbon atoms, more preferably has 2 to 20 carbon atoms, and particularlypreferably has 2 to 10 carbon atoms, and examples thereof include vinyl,allyl, 1-propenyl, 1-isopropenyl, 1-butenyl, 2-butenyl, and 3-pentenyl.

The alkynyl group represented by R^(S1) to R^(S5) has 2 to 30 carbonatoms, more preferably has 2 to 20 carbon atoms, and particularlypreferably has 2 to 10 carbon atoms, and examples thereof includeethynyl, propargyl, 1-propynyl, and 3-pentynyl.

The perfluoroalkyl group represented by R^(S1) to R^(S5) includes agroup obtained by substituting all the hydrogen atoms in theabove-mentioned alkyl group with fluorine atoms.

The aryl group represented by R^(S1) to R^(S5) is preferably asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, andexamples thereof include a phenyl group, a tolyl group, a biphenylgroup, and a terphenyl group.

The heteroaryl group represented by R^(S1) to R^(S5) is preferably aheteroaryl group having 5 to 8 carbon atoms, more preferably asubstituted or unsubstituted 5- or 6-membered heteroaryl group, andexamples thereof include a pyridyl group, a pyrazinyl group, apyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinylgroup, an isoquinolinyl group, a quinazolinyl group, a cinnolinyl group,a phthalazinyl group, a quinoxalinyl group, a pyrrolyl group, an indolylgroup, a furyl group, a benzofuryl group, a thienyl group, abenzothienyl group, a pyrazolyl group, an imidazolyl group, abenzimidazolyl group, a triazolyl group, an oxazolyl group, abenzoxazolyl group, a thiazolyl group, a benzothiazolyl group,anisothiazolyl group, a benzisothiazolyl group, a thiadiazolyl group, anisoxazolyl group, a benzisoxazolyl group, a pyrrolidinyl group, apiperidinyl group, a piperazinyl group, an imidazolidinyl group, athiazolinyl group, a sulfolanyl group, a carbazolyl group, adibenzofuryl group, a dibenzothienyl group, and a pyridoindolyl group.Preferred examples thereof are a pyridyl group, a pyrimidinyl group, animidazolyl group, and a thienyl group, and more preferred examplesthereof are a pyridyl group and a pyrimidinyl group.

R^(S1) to R^(S5) are each preferably a hydrogen atom, an alkyl group, acyano group, a trifluoromethyl group, a perfluoroalkyl group, adialkylamino group, a fluoro group, an aryl group, or a heteroarylgroup, more preferably a hydrogen atom, an alkyl group, a cyano group, atrifluoromethyl group, a fluoro group, or an aryl group, and still morepreferably a hydrogen atom, an alkyl group, or an aryl group. Thesubstituent Z is preferably an alkyl group, an alkoxy group, a fluorogroup, a cyano group, or a dialkylamino group, and more preferably ahydrogen atom or an alkyl group.

Any two of R^(S1) to R^(S5) may be bonded to each other to form a fused4- to 7-membered ring, the fused 4- to 7-membered ring is cycloalkyl,aryl, or heteroaryl, and the fused 4- to 7-membered ring may furtherhave a substituent Z. The definitions and the preferred ranges of theformed cycloalkyl, aryl and heteroaryl are the same as the cycloalkylgroup, the aryl group, and the heteroaryl group defined in R^(S1) toR^(S5).

In the case where the compound represented by the general formula (M-1)is used in a hole transporting layer, the compound represented by thegeneral formula (M-1) is preferably contained in an amount of 50% bymass to 100% by mass, more preferably contained in an amount of 80% bymass to 100% by mass, and particularly preferably contained in an amountof 95% by mass to 100% by mass.

In addition, in the case where the compound represented by the generalformula (M-1) is used in a plurality of organic layers, the compound ispreferably contained in each layer within the above range.

Only one kind of the compound represented by the general formula (M-1)may be contained, in any one of organic layers, or a plurality ofcompounds represented by the general formula (M-1) may be contained incombination of any proportion thereof.

The thickness of the hole transporting layer containing the compoundrepresented by the general formula (M-1) is preferably from 1 nm to 500nm, more preferably from 3 nm to 200 nm, and still more preferably from5 nm to 100 nm. In addition, the hole transporting layer is preferablyprovided in contact with the light emitting layer.

The minimum excited triplet (T₁) energy in the film state of thecompound represented by the general formula (M-1) is preferably from1.77 eV (40 kcal/mol) to 3.51 eV (81 kcal/mol), and more preferably from2.39 eV (55 kcal/mol) to 3.25 eV (75 kcal/mol). In the organicelectroluminescent element of the present invention, it is preferablethat T₁ energy of the compound represented by the general formula (M-1)be more than T₁ energy of the above-mentioned phosphorescent lightemitting material, from the viewpoint of luminous efficiency. Inparticular when the luminescent color from the organicelectroluminescent element is green (the light emission peak wavelengthis from 490 nm to 580 nm), from the viewpoint of luminous efficiency, T₁energy is more preferably from 2.39 eV (55 kcal/mol) to 2.82 eV (65kcal/mol).

The hydrogen atoms constituting the general formula (M-1) includehydrogen isotopes (deuterium and the like). In this case, all thehydrogen atoms in the compound may be substituted with the hydrogenisotope atoms, or the compound may be a mixture in which a part of thecompound contains hydrogen isotopes.

The compound represented by the general formula (M-1) can be synthesizedby combining various known synthetic methods. Most commonly, for thecarbazole compound, a synthetic method may be exemplified in which afused compound of an arylhydradine and a cyclohexane derivative issubjected to the Aza-Cope rearrangement reaction, and thereafterconverted into an aromatic compound by dehydrogenating (written by L. F.Tieze and Th. Eicher, translated by Takano and Ogasawara, Seimitsu YuukiGousei, p. 339 (Nankodo Co., Ltd.)). For a coupling reaction of theresulting carbazole compound with a halogenated aryl compound using apalladium catalyst, a method is exemplified which is described inTetrahedron Letters, vol. 39, p. 617 (1998), vol. 39, p. 2367 (1998),vol. 40, p. 6393 (1999), and the like. The reaction temperature and thereaction time are not particularly limited and the conditions describedin the above documents may be applied.

The compound represented by the general formula (M-1) is preferablyformed into a thin film by a vacuum vapor deposition process, but a wetprocess such as a solution coating can be suitably used. The molecularweight of the compound is preferably 2000 or less, more preferably 1200or less, and particularly preferably 800 or less, from the viewpoint ofdeposition suitability and solubility. In terms of the depositionsuitability, too small molecular weight causes decrease of the vaporpressure, thereby inhibiting the conversion from the vapor phase to thesolid phase, so that it become difficult to form the organic layer.Accordingly, the molecular weight is preferably 250 or more, andparticularly preferably 300 or more.

Specific examples of the compound represented by the general formula(M-1) are shown below, but the present invention is not limited thereto.

(B) Organic Layer Preferably Disposed Between Cathode and Light EmittingLayer

Next, the (B) organic layer preferably disposed between the cathode andthe light emitting layer will be described.

(B-1) Electron Injecting Layer and Electron Transporting Layer

The electron injecting layer and the electron transporting layer arelayers having a function of receiving electrons from the cathode or thecathode side and transporting them to the anode side. The electroninjecting material and the electron transporting material used in theselayers may be either a low-molecular compound or a high-molecularcompound.

As the electron transporting material, the compound represented by thegeneral formula (1) can be used. As other electron transportingmaterials, any one of compounds selected from pyridine derivatives,quinoline derivatives, pyrimidine derivatives, pyrazine derivatives,phthalazine derivatives, phenanthroline derivatives, triazinederivatives, triazole derivatives, oxazole derivatives, oxadiazolederivatives, imidazole derivatives, benzimidazole derivatives,imidazopyridine derivatives, fluorenone derivatives,anthraquinodimethane derivatives, anthrone derivatives, diphenylquinonederivatives, thiopyranedioxide derivatives, carbodiimide derivatives,fluorenylidenemethane derivatives, distyrylpyrazine derivatives,aromatic ring tetracarboxylic acid anhydrides of naphthalene andperylene, phthalocyanine derivatives, various metal complexes typifiedby metal complexes of 8-quinolinol derivatives, metal phthalocyanine andmetal complexes having benzoxazole or benzothiazole as a ligand thereof,organic silane derivatives typified by silole, and hydrocarbon compoundswith fused rings such as naphthalene, anthracene, phenanthrene,triphenylene, and pyrene is preferred, and any one of compounds selectedfrom pyridine derivatives, benzimidazole derivatives, imidazopyridinederivatives, metal complexes, and hydrocarbon compounds with fused ringsare more preferred.

From the viewpoint of decreasing the driving voltage, the thickness ofeach of the electron injecting layer and the electron transporting layeris preferably 500 nm or less.

The thickness of the electron transporting layer is preferably from 1 nmto 500 nm, more preferably from 5 nm to 200 nm, and still morepreferably from 10 nm to 100 nm. In addition, the thickness of theelectron injecting layer is preferably from 0.1 nm to 200 nm, morepreferably from 0.2 nm to 100 nm, and still more preferably from 0.5 nmto 50 nm.

The electron injecting layer and the electron transporting layer mayhave either a single layer structure composed of one kind or two or morekinds of materials selected from the above-exemplified materials or amultilayer structure composed of a plurality of layers having the samecomposition or different compositions.

The electron injecting layer preferably contains an electron donatingdopant. By incorporating the electron donating dopant into the electroninjecting layer, for example, there are brought such effects that theelectron injecting properties are enhanced, that the driving voltage islowered, and that the efficiency is enhanced. The electron donatingdopant may be any one of organic materials and inorganic materials aslong as it is capable of giving electrons to the material to be doped togenerate radical anions. Examples thereof include dihydroimidazolecompounds such as tetrathiafulvalene (TTF), tetrathianaphthacene (TTT),and bis-[1,3-diethyl-2-methyl-1,2-dihydrobenzimidazolyl], lithium, andcesium.

The electron donating dopant in the electron injecting layer iscontained in the amount of preferably from 0.01% by mass to 50% by mass,more preferably from 0.1% by mass to 40% by mass, and still morepreferably from 0.5% by mass to 30% by mass, with respect to the totalmass of the compounds forming the electron injecting layer.

(B-2) Hole Blocking Layer

The hole blocking layer is a layer having a function of preventingholes, which have been transported from the anode side to the lightemitting layer, from passing through to the cathode side. In the presentinvention, the hole blocking layer can be provided as an organic layeradjacent to the light emitting layer on the cathode side.

In order to inhibit the energy transfer of excitons generated in thelight emitting layer to prevent degradation of luminous efficiency, T₁energy in the film state of the organic compound constituting the holeblocking layer is preferably higher than the T₁ energy of the lightemitting material.

As an example of the organic compound constituting the hole blockinglayer, for example, the compound represented by the general formula (1)can be used.

Examples of the organic compounds constituting the hole blocking layer,other than the compound represented by the general formula (1), includealuminum complexes such as aluminum (III) tris-8-hydroxyquinoline(abbreviated as Alq) and aluminum (III) bis(2-methyl-8-quinolinato)4-phenylphenolate (abbreviated as Balq), triazole derivatives, andphenanthroline derivatives such as2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (abbreviated as BCP). Inthe present invention, the function of the hole blocking layer is notlimited to the function of actually blocking the holes, and the holeblocking layer may have a function to prevent the excitons in the lightemitting layer from diffusing to the electron transporting layer, or afunction to block energy transfer quenching. The compound of the presentinvention can be preferably applied to the hole blocking layer.

The thickness of the hole blocking layer is preferably from 1 nm to 500nm, more preferably from 3 nm to 100 nm, and still more preferably from5 nm to 50 nm.

The hole blocking layer may have either a single layer structurecomposed of one kind or two or more kinds of materials selected from theabove-exemplified materials or a multilayer structure composed of aplurality of layers having the same composition or differentcompositions.

The material which is used in the hole blocking layer preferably hashigher T₁ energy than that of the phosphorescent light emitting materialin view of color purity, luminous efficiency, and driving durability.

(B-3) Material Particularly Preferably Used in Organic Layer which isPreferably Disposed Between Cathode and Light Emitting Layer

For the organic electroluminescent element of the present invention,examples of the material which is particularly preferably used in thematerials for the (B) organic layer which is preferably disposed betweenthe cathode and the light emitting layer include the compoundrepresented by the general formula (1), an aromatic hydrocarbon compound(in particular, a compound represented by the following general formula(Tp-1)), and a compound represented by the following general formula(O-1).

The aromatic hydrocarbon compound and a compound represented by thegeneral formula (O-1) will be described below.

[Aromatic Hydrocarbon Compound]

The aromatic hydrocarbon compound is preferably contained in an organiclayer that is located between the light emitting layer and the cathodeand adjacent to the light emitting layer, but is not limited in the useand may be further contained in any layer of the organic layers. Thelayer into which the aromatic hydrocarbon compound is introduced is anyone of a light emitting layer, a hole injecting layer, a holetransporting layer, an electron transporting layer, an electroninjecting layer, an exciton blocking layer, and a charge blocking layer,or the compound may be contained in a plurality of layers.

The organic layer that is located between the light emitting layer andthe cathode and adjacent to the light emitting layer, into which thearomatic hydrocarbon compound is contained, is preferably a blockinglayer (a hole blocking layer or an exciton blocking layer) or anelectron transporting layer, and more preferably an electrontransporting layer.

In the case where the aromatic hydrocarbon compound is contained in alayer other than the light emitting layer, the compound is preferablycontained in an amount of 70% by mass to 100% by mass, and morepreferably 85% by mass to 100% by mass. In the case where the aromatichydrocarbon compound is contained in the light emitting layer, thecompound is preferably contained in an amount of 0.1% by mass to 99% bymass, more preferably contained in an amount of 1% by mass to 95% bymass, and more preferably contained in an amount of 10% by mass to 95%by mass, with respect to the total mass of the light emitting layer.

As the aromatic hydrocarbon compound, a hydrocarbon compound which has amolecular weight of 400 to 1200 and has a fused polycyclic skeletonhaving a total carbon number of 13 to 22 is preferably used. The fusedpolycyclic skeleton having a total carbon number of 13 to 22 ispreferably any one of fluorene, anthracene, phenanthrene, tetracene,chrysene, pentacene, pyrene, perylene, and triphenylene, more preferablyfrom the viewpoint of the T₁, a fluorene, triphenylene, andphenanthrene, still more preferably from the viewpoint of compoundstability and electron injecting and transporting properties,triphenylene, and particularly preferably a compound represented by thefollowing general formula (Tp-1).

The hydrocarbon compound represented by the general formula (Tp-1) has amolecular weight of preferably 400 to 1200, more preferably 400 to 1100,and still more preferably 400 to 1000. When the molecular weight is 400or more, an amorphous thin film of good quality can be formed, and themolecular weight of 1200 or less is preferred in terms of solubility ina solvent and applicability to sublimation and deposition suitability.

The hydrocarbon compound represented by the general formula (Tp-1) isnot limited in the use, and may be contained not only in the organiclayer adjacent to the light emitting layer but in any layer in theorganic layers.

In the general formula (Tp-1), R¹² to R²³ each independently represent ahydrogen atom, an alkyl group, a phenyl group, a fluorenyl group, anaphthyl group, or a triphenylenyl group (these groups may be furthersubstituted with an alkyl group, a phenyl group, a fluorenyl group, anaphthyl group, or a triphenylenyl group), provided that not all of R¹²to R²³ are a hydrogen atom.

Examples of the alkyl group represented by R¹² to R²³ include a methylgroup, an ethyl group, an isopropyl group, an n-butyl group, atert-butyl group, an n-octyl group, an n-decyl group, an n-hexadecylgroup, a cyclopropyl group, a cyclopentyl group, and a cyclohexyl group,preferably a methyl group, an ethyl group, an isopropyl group, atert-butyl group, and a cyclohexyl group, and more preferably a methylgroup, ethyl group, and a tert-butyl group, each of which may besubstituted or unsubstituted.

R¹² to R²³ may be each preferably substituted with an alkyl group having1 to 4 carbon atoms, a phenyl group, a fluorenyl group, a naphthylgroup, or a triphenylenyl group (which may be further substituted withan alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, ora triphenylenyl group), and still more preferably a phenyl group, afluorenyl group, a naphthyl group, or a triphenylenyl group.

R¹² to R²³ are each particularly preferably a benzene ring which may besubstituted with a phenyl group, a fluorenyl group, a naphthyl group, ora triphenylenyl group (which may further substituted with an alkylgroup, a phenyl group, a fluorenyl group, a naphthyl group, or atriphenylenyl group).

The total number of the aryl rings in the general formula (Tp-1) ispreferably from 2 to 8, and more preferably from 3 to 5. When the arylring number is within this range, it is possible to form an amorphousthin film of high quality and to achieve good solubility in a solvent,applicability to sublimation, and deposition suitability.

R¹² to R²³ preferably each independently have a total carbon number of20 to 50, and more preferably a total carbon number of 20 to 36. Whenthe total carbon number is within this range, it is possible to form anamorphous thin film of high quality and to achieve good solubility in asolvent, applicability to sublimation, and deposition suitability.

The hydrocarbon compound represented by the general formula (Tp-1) ispreferably a hydrocarbon compound represented by the following generalformula (Tp-2).

In the general formula (Tp-2), a plurality of Ar¹¹s are the same, andeach represent an alkyl group, a phenyl group, a fluorenyl group, anaphthyl group, or a triphenylenyl group (these groups may be furthersubstituted with an alkyl group, a phenyl group, a fluorenyl group, anaphthyl group, or a triphenylenyl group).

The hydrogen atom, the alkyl group, the phenyl group, the fluorenylgroup, the naphthyl group, or the triphenylenyl group represented byAr¹¹ (these groups may be further substituted with an alkyl group, aphenyl group, a fluorenyl group, a naphthyl group, or a triphenylenylgroup) has the same definitions as enumerated for R¹² to R²³, andpreferred ones are also the same.

The hydrocarbon compound represented by the general formula (Tp-1) isalso preferably a hydrocarbon compound represented by the followinggeneral formula (Tp-3).

In the general formula (Tp-3), L represents an alkyl group, a phenylgroup, a fluorenyl group, a naphthyl group, or a triphenylenyl group(these groups may be further substituted with an alkyl group, a phenylgroup, a fluorenyl group, a naphthyl group, or a triphenylenyl group),or an n-valent linking group formed by a combination thereof. nrepresents an integer of 2 to 6.

The alkyl group, the phenyl group, the fluorenyl group, the naphthylgroup, or the triphenylenyl group, which forms the n-valent linkinggroup represented by L, has the same definitions as enumerated for R¹²to R²³.

L is preferably an n-valent linking group formed of a benzene ring or afluorene ring which may be substituted by an alkyl group or a benzenering, or a combination thereof.

Specific preferred examples of L are listed below, but L is not limitedthereto. In the specific examples, the group is bonded at * to atriphenylene ring.

n is preferably from 2 to 5, and more preferably from 2 to 4.

The compound represented by the general formula (Tp-1) is preferably acompound represented by the following general formula (Tp-4).

(In the general formula (Tp-4), A^(A1) to A^(A12) each independentlyrepresent CR⁴⁰⁰ or a nitrogen atom. n⁴⁰¹ represents an integer of 0 to8. In the case where n⁴⁰¹ is 0, the ring represented by A^(A1) to A^(A6)represents a single bond between the triphenylene ring and the ringrepresented by A^(A7) to A^(A12). In the case where n⁴⁰¹ is from 2 to 6,a plurality of rings represented by A^(A1) to A^(A6) may be differentfor each appearance, and a plurality of linking modes between the ringsmay be different for each appearance.)

Incidentally, in the present invention, the hydrogen atoms in thedescription of the general formula (Tp-4) include isotopes (a deuteriumatom and the like), and any atoms constituting the further substituentalso include the isotopes thereof.

In the general formula (Tp-4), R⁴¹¹ to R⁴²¹ each independently representa hydrogen atom, an alkyl group, a phenyl group, a fluorenyl group, anaphthyl group, or a triphenylenyl group (which may be furthersubstituted with an alkyl group, a phenyl group, a fluorenyl group, anaphthyl group, or a triphenylenyl group).

R⁴¹¹ to R⁴²¹ are each preferably a hydrogen atom, an alkyl group having1 to 4 carbon atoms, a phenyl group, a fluorenyl group, a naphthylgroup, or a triphenylenyl group (which may be further substituted withan alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, ora triphenylenyl group), more preferably a hydrogen atom or a phenylgroup (the phenyl group may be substituted with an alkyl group, a phenylgroup, a fluorenyl group, a naphthyl group, or a triphenylenyl group),and particularly preferably a hydrogen atom.

A^(A1) to A^(A12) are each preferably CR⁴⁰⁰.

In the general formula (Tp-4), the substituent represented by R⁴⁰⁰preferably represents a hydrogen atom, an alkyl group having 1 to 4carbon atoms, a phenyl group, a fluorenyl group, a naphthyl group, or atriphenylenyl group (which may be further substituted with an alkylgroup, a phenyl group, a fluorenyl group, a naphthyl group, or atriphenylenyl group). A plurality of R⁴⁰⁰s may be different from eachother.

Preferably, R⁴⁰⁰ is preferably a hydrogen atom, an alkyl group having 1to 4 carbon atoms, a phenyl group, a fluorenyl group, a naphthyl group,or a triphenylenyl group (which may be further substituted with an alkylgroup, a phenyl group, a fluorenyl group, a naphthyl group, or atriphenylenyl group), more preferably a hydrogen atom, an alkyl grouphaving 1 to 4 carbon atoms, a phenyl group (the phenyl group may besubstituted with an alkyl group, a phenyl group, a fluorenyl group, anaphthyl group, or a triphenylenyl group), and particularly preferably ahydrogen atom, an alkyl group having 1 to 4 carbon atoms, a phenyl group(the phenyl group may be substituted with an alkyl group, a phenylgroup, a fluorenyl group, a naphthyl group, or a triphenylenyl group).

n⁴⁰¹ is preferably an integer of 0 to 5, more preferably an integer of 1to 5, and particularly preferably 2 to 4.

n⁴⁰¹ is an integer of 1 or more, and in the case where the linkingposition to the ring represented by A^(A7) to A^(A12) is A^(A3), fromthe viewpoint of luminous efficiency, the substituent represented byA^(A4) or A^(A5) is CR⁴⁰⁰, and R⁴⁰⁰ is preferably an alkyl group having1 to 4 carbon atoms or a phenyl group, more preferably an alkyl grouphaving 1 to 4 carbon atoms, and particularly preferably a methyl group.

In the general formula (Tp-4), among the 6-membered aromatic ringsconstituted of A^(A1) to A^(A12), the number of the ring containing anitrogen atom is preferably at most one, and more preferably zero. Inthe general formula (Tp-4), the connection of the 6-membered aromaticrings constituted of A^(A1) to A^(A12) has no restriction, but the ringspreferably are connected on meta- or para-positions. Further, withregard to the compound represented by the general formula (Tp-4), thenumber of the aromatic rings which are sequentially connected on theirpara-positions is preferably three or less, including the phenyl ringwhich is a partial structure of the fused ring constituting thetriphenylene ring.

In the case where the hydrocarbon compound represented by the generalformula (Tp-1) is used in a host material of a light emitting layer orin a charge transporting material of a layer adjacent to the lightemitting layer, in an organic electroluminescent element, when theenergy gap in the thin film state (in the case of the light emittingmaterial being a phosphorescent light emitting material, which is theminimum excited triplet (T₁) energy in the thin film state) is largerthan in the light emission material, the quench of the light emission isprevented, which is advantageous in enhancing the efficiency. On theother hand, from the viewpoint of chemical stability of the compound, itis preferable that an energy gap and T₁ energy are not too large. The T₁energy in the film state of the hydrocarbon compound represented by thegeneral formula (Tp-1) is preferably from 1.77 eV (40 kcal/mol) to 3.51eV (81 kcal/mol), and more preferably from 2.39 eV (55 kcal/mol) to 3.25eV (75 kcal/mol). In the organic electroluminescent element according tothe present invention, it is preferable from the viewpoint of luminousefficiency that the T₁ energy of the compound represented by the generalformula (Tp-1) be more than the T₁ energy of the above-mentionedphosphorescent light emitting material. In particular, in the case wherethe luminescent color from the organic electroluminescent element isgreen (the light emission peak wavelength is from 490 nm to 580 nm), itis more preferred from the viewpoint of luminous efficiency that the T₁energy is from 2.39 eV (55 kcal/mol) to 2.82 eV (65 kcal/mol).

The T₁ energy of the hydrocarbon compound represented by the generalformula (Tp-1) can be determined by the same method as in thedescription of the general formula (1) above.

From the viewpoint of stable operation of the organic electroluminescentelement, when being driven at a high temperature, or against the heatgeneration during the element driving, the glass transition temperature(Tg) of the hydrocarbon compound according to the present invention ispreferably from 80° C. to 400° C., more preferably from 100° C. to 400°C., and still more preferably from 120° C. to 400° C.

Specific examples of the hydrocarbon compound represented by the generalformula (Tp-1) are listed below, but the hydrocarbon compound used inthe present invention is not to be limited thereto.

The compounds exemplified above as the hydrocarbon compound representedby general formula (Tp-1) can be synthesized by the methods described inWO05/013388, WO06/130598, WO09/021,107, US2009/0009065, WO09/008,311,and WO04/018587.

After the synthesis, it is preferable that the product be purified bycolumn chromatography, recrystallization, and the like, and thenpurified by sublimation purification. By sublimation purification, it ispossible not only to separate the organic impurities but also toeffectively remove the inorganic salts, remaining solvent, and the like.

[Compound Represented by General Formula (O-1)]

As a material particularly preferably used for the material of the (B)organic layer which is preferably disposed between the cathode and thelight emitting layer, the compound represented by the following generalformula (O-1) is preferably used, from the viewpoint of the efficiencyand the driving voltage of the organic electroluminescent element. Thegeneral formula (O-1) will be described below.

In the general formula (O-1), R^(O1) represents an alkyl group, an arylgroup, or a heteroaryl group. A^(O1) to A^(O4) each independentlyrepresent C—R^(A) or a nitrogen atom. R^(A) represents a hydrogen atom,an alkyl group, an aryl group, or a heteroaryl group, and a plurality ofR^(A)s may be the same as or different from each other. L^(O1)represents a divalent to hexavalent linking group composed of an arylring or a heteroaryl ring. n^(O1) represents an integer of 2 to 6.

R^(O0) represents an alkyl group (preferably having 1 to 8 carbonatoms), an aryl group (preferably having 6 to 30 carbon atoms), or aheteroaryl group (preferably having 4 to 12 carbon atoms), which mayhave the Substituent Group A as described above. R^(O1) is preferably anaryl group or a heteroaryl group, and more preferably an aryl group.Preferred examples of the substituent in the case where the aryl groupof R^(O1) has a substituent include an alkyl group, an aryl group, and acyano group. Among them, an alkyl group or an aryl group are morepreferred, with an aryl group being still more preferred. In the casewhere the aryl group of R^(O1) has a plurality of substituents, aplurality of substituents may be bonded to each other to form a 5- or6-membered ring. The aryl group of R^(O1) is preferably a phenyl groupwhich may have the Substituent Group A as described above, morepreferably a phenyl group which may be substituted with an alkyl groupor an aryl group, and still more preferably an unsubstituted phenylgroup or a 2-phenylphenyl group.

A^(O1) to A^(O4) each independently represent C—R^(A) or a nitrogenatom. It is preferable that from zero to two of A^(O1) to A^(O4) be anitrogen atom, and it is more preferable that zero or one of A^(O1) toA^(O4) be a nitrogen atom. It is preferable that all of A^(O1) to A_(O4)be C—R^(A), and A^(O1) be a nitrogen atom, and A^(O2) to A^(O4) beC—R^(A), it is more preferable that A^(O0) be a nitrogen atom, andA^(O2) to A^(O4) be C—R^(A), and it is still more preferable that A^(O1)be a nitrogen atom, A^(O2) to A^(O4) be C—R^(A), and R^(As) be all ahydrogen atom.

R^(A) represents a hydrogen atom, an alkyl group (preferably having 1 to8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms),or a heteroaryl group (preferably having 4 to 12 carbon atoms), and mayhave the above-mentioned substituent Z′. In addition, a plurality ofR^(A)s may be the same as or different from one another. R^(A) ispreferably a hydrogen atom or an alkyl group, and more preferably ahydrogen atom.

L^(O1) represents a divalent to hexavalent linking group composed of anaryl ring (preferably having 6 to 30 carbon atoms) or a heteroaryl ring(preferably having 4 to 12 carbon atoms). L^(O1) is preferably anarylene group, a heteroarylene group, an aryltriyl group, or aheteroaryltriyl group, more preferably a phenylene group, a biphenylenegroup, or a benzenetriyl group, and still more preferably a biphenylenegroup or a benzenetriyl group. L^(O1) may have the above-mentionedsubstituent Z′, and in the case where L^(O1) has a substituent, thesubstituent is preferably an alkyl group, an aryl group, or a cyanogroup. Specific examples of L^(O1) include the following.

n^(O1) represents an integer of 2 to 6, preferably an integer of 2 to 4,and more preferably 2 or 3. n^(O1) is most preferably 3 from theviewpoint of efficiency of the organic electroluminescent element, orn^(O1) is most preferably 2 from the viewpoint of durability of theorganic electroluminescent element.

The compound represented by the general formula (O-1) is preferably acompound represented by the following general formula (O-2).

In the general formula (O-2), R^(O1)s each independently represent analkyl group, an aryl group, or a heteroaryl group. R^(O1) to R^(O4) eachindependently represent a hydrogen atom, an alkyl group, an aryl group,or a heteroaryl group. A^(O1) to A^(O4) each independently representC—R^(A) or a nitrogen atom. R^(A) represents a hydrogen atom, an alkylgroup, an aryl group, or a heteroaryl group, and a plurality of R^(A)smay be the same as or different from one another.

R^(O1) and A^(O1) to A^(O4) have the same definitions as R^(O1) andA^(O1) to A^(O4) in the general formula (O-1) described above, and thepreferred ranges thereof are also the same.

R^(O2) to R^(O4) each independently represent a hydrogen atom, an alkylgroup (preferably having 1 to 8 carbon atoms), an aryl group (preferablyhaving 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4to 12 carbon atoms), and these groups may have a substituent selectedfrom the Substituent Group A described above. R^(O2) to R^(O4) arepreferably a hydrogen atom, an alkyl group or an aryl group, morepreferably a hydrogen atom or an aryl group, and most preferably ahydrogen atom.

The glass transition temperature (Tg) of the compound represented by thegeneral formula (O-1) is preferably from 100° C. to 400° C., morepreferably from 120° C. to 400° C., still more preferably from 140° C.to 400° C., from the viewpoint of stability at the time of storage at ahigh temperature, or stable operation during driving at a hightemperature against heat generation during driving.

Specific examples of the compound represented by the general formula(O-1) will be shown below, but the compound used in the presentinvention is not limited thereto.

The compound represented by the general formula (O-1) can be synthesizedby the method described in JP-A-2001-335776. After the synthesis, it ispreferable that the product is purified by column chromatography,recrystallization, reprecipitation, and then purified by sublimationpurification. By sublimation purification, it is possible not only toseparate organic impurities but also to effectively remove inorganicsalts, remaining solvent, moisture, or the like.

In the organic electroluminescent element of the present invention, thecompound represented by the general formula (O-1) is preferablycontained in an organic layer between the light emitting layer and thecathode, and more preferably contained a layer adjacent to the lightemitting layer on the cathode side.

<Protective Layer>

In the present invention, the entirety of the organic electroluminescentelement may be protected by a protective layer.

For the protective layer, the detailed description in paragraph Nos.[0169] to [0170] of JP-A-2008-270736 can be applied to the presentinvention. Incidentally, the materials for the protective layer may beeither an inorganic material or an organic material.

<Sealing Enclosure>

For the organic electroluminescent element of the present invention, theentirety of the element may be sealed using a sealing enclosure.

For the sealing enclosure, the detailed description in paragraph No.[0171] of JP-A-2008-270736 can be applied to the present invention.

<Driving Method>

The organic electroluminescent element of the present invention can emitlight by applying a direct current (it may include an alternate currentcomponent, if desired) voltage (usually from 2 volts to 15 volts) or adirect current between the anode and the cathode.

As a driving method of the organic electroluminescent element of thepresent invention, driving methods described in JP-A-2-148687,JP-A-6-301355, JP-A-5-29080, JP-A-7-134558, JP-A-8-234685, andJP-A-8-241047, Japanese Patent No. 2784615, and U.S. Pat. Nos. 5,828,429and 6,023,308 can be applied.

The external quantum efficiency of the organic electroluminescentelement of the present invention is preferably 7% or more, and morepreferably 10% or more. As for the numerical value of the externalquantum efficiency, a maximum value of the external quantum efficiencyobtained when the organic electroluminescent element is driven at 20°C., or a value of the external quantum efficiency in the vicinity offrom 300 cd/m² to 400 cd/m² obtained when the element is driven at 20°C. can be employed.

The internal quantum efficiency of the organic electroluminescentelement of the present invention is preferably 30% or more, morepreferably 50% or more, and still more preferably 70% or more. Theinternal quantum efficiency of the element is calculated by dividing theexternal quantum efficiency by the light extraction efficiency. Thoughthe light extraction efficiency in usual organic EL elements is about20%, by adjusting the shape of a substrate, the shape of an electrode,the film thickness of an organic layer, the film thickness of aninorganic layer, the refractive index of an organic layer, therefractive index of an inorganic layer, or the like, it is possible toincrease the light extraction efficiency to 2C % or more.

<Light Emitting Wavelength>

The organic electroluminescent element of the present invention has nolimitation in its light emitting wavelength, and may be used for redlight emission, green light emission, or blue light emission among thethree primary colors of light. Above all, the organic electroluminescentelement of the present invention preferably have a emission peakwavelength of 400 nm to 700 nm from the viewpoint of luminous efficiencyin view of the minimum excision triplet (T₁) energy of the compoundrepresented by the general formula (1).

Specifically, in the organic electroluminescent element of the presentinvention, in the case of using the compound represented by the generalformula (1) as a host material of the light emitting layer, or as anelectron transporting material of the electron transporting layer or thehole blocking layer, the light emission peak wavelength of the guestmaterial is preferably from 400 nm to 700 nm, more preferably from 450nm to 650 nm, and particularly preferably from 480 nm to 550 nm.

<Use of Organic Electroluminescent Element of the Present Invention>

The organic electroluminescent element according to the presentinvention can be suitably used for display elements, displays,backlights, electrophotography, illumination light sources, recordinglight sources, exposure light sources, readout light sources, signs,billboards, interior decorations, optical communications, and the like.In particular, it is preferably used for devices to be driven in aregion of high-intensity luminescence, such as a light emitting device,an illumination device, and a display device.

[Light Emitting Device]

The light emitting device of the present invention may include theorganic electroluminescent element of the present invention.

Next, the light emitting device of the present invention will bedescribed with reference to FIG. 2.

FIG. 2 is a cross-sectional view schematically showing one example ofthe light emitting device of the present invention. The light emittingdevice 20 in FIG. 2 includes a transparent substrate 2 (supportingsubstrate), an organic electroluminescent element 10, a sealingenclosure 16, and the like.

The organic electroluminescent element 10 is formed by laminating ananode (first electrode) 3, an organic layer 11, and a cathode (secondelectrode) 9 in this order on a substrate 2. In addition, a protectivelayer 12 is laminated on the cathode 9, and a sealing enclosure 16 isfurther provided via an adhesive layer 14 on the protective layer 12.Incidentally, a part of each of the electrodes 3 and 9, a diaphragm, aninsulating layer, and the like are omitted.

Here, as the adhesive layer 14, a photocurable adhesive such as an epoxyresin, or a thermosetting adhesive can be used, and for example, athermosetting adhesive sheet may also be used.

The light emitting device of the present invention is not particularlylimited in its use, and it can be used as not only an illuminationdevice but also a display device of a television set, a personalcomputer, a mobile phone, electronic paper, or the like.

[Illumination Device]

The illumination device of the present invention includes the organicelectroluminescent element of the present invention.

Next, the illumination device of the present invention will be describedwith reference to FIG. 3.

FIG. 3 is a cross-sectional view schematically showing one example ofthe illumination device of the present invention. The illuminationdevice 40 of the present invention includes, as shown in FIG. 3, theabove-described organic EL element 10 and a light scattering member 30.More specifically, the illumination device 40 is configured such thatthe substrate 2 of the organic EL element 10 and the light scatteringmember 30 are in contact with each other.

The light scattering member 30 is not particularly limited as long as itcan scatter light, but in FIG. 3, a member obtained by dispersing fineparticles 32 in a transparent substrate 31 is used. Suitable examples ofthe transparent substrate 31 include a glass substrate, and suitableexamples of the fine particles 32 include transparent resin fineparticles. As the glass substrate and the transparent resin fineparticles, a known product can be used for both. In such an illuminationdevice 40, when light emitted from the organic electroluminescentelement 10 is incident on the light incident surface 30A of thescattering member 30, the incident light is scattered by the lightscattering member 30 and the scattered light is output as illuminatinglight from the light output surface 30B.

[Display Device]

The display device of the present invention may include the organicelectroluminescent element of the present invention.

The display device of the present invention may be used for, forexample, a display device of a television set, a personal computer, amobile phone, electronic paper, or the like.

EXAMPLES

Hereinafter, the characteristic features of the present invention willbe described in more detail with reference to Examples. The materials,use amounts, ratios, treatment details, treatment procedures, and thelike shown in the following Examples can be appropriately modified sofar as the gist of the present invention is not deviated. Accordingly,the scope of the present invention is not limited to the specificexamples shown below.

Example 1 Synthesis of Compound No O-10-10

According to the scheme, a compound No O-10-10 was synthesized.

The obtained compound No O-10-10 was subjected to MASS spectrummeasurement to check the peaks of [M+H]⁺.

<Fabrication and Evaluation of Organic Electroluminescent Element>

The organic materials used in the preparation of the organicelectroluminescent element were all subjected to sublimationpurification. The compounds used in Comparative Examples and Examplesare shown below.

Comparative Compound 1: Compound (4-3) described in WO2010/131855

Comparative Compound 2: Compound (I) described in JP-A-2010-087496

Comparative Compound 3: Compound (54) described in JP-A-2010-87496

Comparative Compound 4: Compound (70) described in JP-A-2010-87496

Comparative Example 1 Fabrication of Anode

A 0.5 mm-thick and 2.5 cm square glass substrate (manufactured byGeomatec Co., Ltd., surface resistance: 10Ω/□) having an ITO filmthereon was put in a cleaning container. After ultrasonic cleaning in2-propanol, the glass substrate was subjected to a UV-ozone treatmentfor 30 minutes.

This was used as an anode (ITO film, transparent anode).

(Lamination of Organic Layers)

On the anode, first to fifth organic layers were sequentially depositedusing the following compounds by a vacuum deposition method. Thecompound structures used in respective layers are shown below together.

First layer: LG101: film thickness: 10 nm

Second layer: NPD: film thickness: 30 nm

Third layer: Comparative Compound 1 (host material) and greenphosphorescent light emitting material GD-1 (guest material) (massratio: 85:15): film thickness: 30 nm

Fourth layer: TpH-18: film thickness: 10 nm

Fifth layer: Alq: film thickness: 40 nm

(Fabrication of Cathode)

On the above lamination, 0.1 nm of lithium fluoride and 200 nm of metalaluminum were deposited in this order to form a cathode.

(Fabrication of Organic Electroluminescent Element)

A lamination which includes the anode and the cathode, and the fiveorganic layers disposed between the anode and the cathode was placed ina glove box purged with nitrogen gas without contact with atmosphericair, and sealed in a glass sealing can using an ultraviolet cureadhesive (XNR5516HV, manufactured by Nagase-Chiba, Ltd.) to obtain anorganic electroluminescent element of Comparative Example 1.

(Evaluation of Organic Electroluminescent Element)

(a) Durability

A DC voltage was applied to the organic electroluminescent element ofComparative Example 1 to allow the element to emit light continuously toattain a luminance of 8000 cd/m² at room temperature, and the timeperiod required for the luminance to go down to 7200 cd/m² was measured.This time period was used as an index of the durability of the organicelectroluminescent element.

Furthermore, in the respective Tables shown below in the respectiveExamples and Comparative Examples as described later, the durability ata time of using the organic electroluminescent element of ComparativeExample 1 was taken as 100 and the element having a relative value ofthe durability of less than 100 was rated as “C”, the element havingthat ranging from 100 to less than 120 as “B”, and the element havingthat of 120 or more as “A”.

Here, a larger number of durability is more preferred.

(b) Driving Voltage

A DC voltage was applied to the organic electroluminescent element ofComparative Example 1 to allow the element to emit light to attain aluminance of 1000 cd/m². The voltage applied at this time was used as anindex of the evaluation of the driving voltage.

Further, in respective Examples and Comparative Examples as describedlater, the applied voltage of the organic electroluminescent element ofComparative Example 1 was taken as 100 and the element having a relativevalue of the voltage of 100 or more was rated as “C”, the element havingthat ranging from 90 to less than 100 as “B”, and the element havingthat of less than 90 as “A”.

Here, a smaller number of driving voltage is more preferred.

Examples A1 to A14 and Comparative Examples 2 to 4

The organic electroluminescent elements in Examples A1 to A14 andComparative Example 2 were obtained by the same procedure as inComparative Example 1, except that the compound of the presentapplication or Comparative Compounds 2 to 4 were used instead ofComparative Compound 1 as a material for the third layer in the organiclayers.

The durability and the driving voltage of these organicelectroluminescent elements were measured by the same method as for theorganic electroluminescent element using the Comparative Compound 1 inComparative Example 1 above, and evaluated in accordance with themeasurement criteria as described above. The results are shown in Table66 below.

TABLE 66 Driving Host material Durability voltage ComparativeComparative Compound 1 — — Example 1 Comparative Comparative Compound 2C C Example 2 Comparative Comparative Compound 3 C C Example 3Comparative Comparative Compound 4 C C Example 4 Example A1 Compound NoO-10-10 A A Example A2 Compound No O-10-40 A A Example A3 Compound NoO-10-22 A A Example A4 Compound No C-10-2 B B Example A5 Compound NoO-12-42 A B Example A6 Compound No N-13-24 B A Example A7 Compound NoO-13-10 A A Example A8 Compound No S-13-18 B A Example A9 Compound NoO-14-4 A B Example A10 Compound No O-14-79 A A Example A11 Compound NoS-15-16 A A Example A12 Compound No O-16-9 B A Example A13 Compound NoS-16-15 B B Example A14 Compound No S-17-12 A A

Comparative Example 5

The organic electroluminescent element of Comparative Example 5 wasfabricated in the same manner as in Comparative Example 1, except thatNPD used in the second layer was changed to HTL-1, GD-1 used in thethird layer was changed to GD-2, TpH-18 used in the fourth layer waschanged to OM-8, and Alq used in the fifth layer was changed to OM-8.The configuration of the organic layers in Comparative Example 5 isshown below.

First layer: LG101, film thickness: 10 nm

Second layer: HTL-1, film thickness: 30 nm

Third layer: Comparative Compound 1 (host material) and greenphosphorescent light emitting material GD-2 (guest material) (massratio: 85:15), film thickness: 30 nm

Fourth layer: OM-8, film thickness: 10 nm

Fifth layer: OM-8, film thickness: 40 nm

Examples B1 to B14 and Comparative Examples 6 to 8

The organic electroluminescent elements of Examples B1 to B14 andComparative Example 4 were obtained in the same manner as in ComparativeExample 5, except that the compound of the present application orComparative Compound 2 was used instead of Comparative Compound 1 as thematerial for the third layer in the organic layers.

The durability and the driving voltage of these organicelectroluminescent elements were measured by the same method as for theorganic electroluminescent element using the Comparative Compound 1 inComparative Example 1 above, and evaluated in accordance with themeasurement criteria as described above. The results are shown in Table67 below.

TABLE 67 Driving Host material Durability voltage ComparativeComparative Compound 1 — — Example 5 Comparative Comparative Compound 2C C Example 6 Comparative Comparative Compound 3 C C Example 7Comparative Comparative Compound 4 C C Example 8 Example B1 Compound NoO-10-10 A A Example B2 Compound No O-10-40 A B Example B3 Compound NoO-10-22 A A Example B4 Compound No C-10-2 B B Example B5 Compound NoO-12-42 A B Example B6 Compound No N-13-24 B B Example B7 Compound NoO-13-10 A A Example B8 Compound No S-13-18 B A Example B9 Compound NoO-14-4 A B Example B10 Compound No O-14-79 A B Example B11 Compound NoS-15-16 A A Example B12 Compound No O-16-9 A A Example B13 Compound NoS-16-15 B A Example B14 Compound No S-17-12 A A

Comparative Example 9

The organic electroluminescent element of Comparative Example 9 wasfabricated in the same manner as in Comparative Example 1, except thatLG101 used in the first layer was changed to GD-1, GD-1 used in thethird layer was changed to a red phosphorescent light emitting materialRD-1, and TpH-18 used in the fourth layer was changed to Alq. Theconfiguration of the organic layers in Comparative Example 9 is shownbelow.

First layer: GD-1, film thickness: 10 nm

Second layer: NPD, film thickness: 30 nm

Third layer: Comparative Compound 1 (host material) and redphosphorescent light emitting material RD-1 (guest material) (massratio: 90:10), film thickness: 30 nm

Fourth layer: Alq, film thickness: 10 nm

Fifth: Alq, film thickness: 40 nm

Examples C1 to C10 and Comparative Examples 10 to 12

The organic electroluminescent elements of Examples C1 to C10 andComparative Examples 10 to 12 were obtained in the same manner as inComparative Example 9, except that, as the material for the third layerin the organic layers, the compound of the present application orComparative Compound 2 was used instead of Comparative Compound 1.

The durability and the driving voltage of these organicelectroluminescent elements were measured by the same method as for theorganic electroluminescent element using the Comparative Compound 1 inComparative Example 1 above, and evaluated in accordance with themeasurement criteria as described above. The results are shown in Table68 below.

TABLE 68 Driving Host material Durability voltage Comparative ExampleComparative Compound 1 — — 9 Comparative Example Comparative Compound 2C C 10 Comparative Example Comparative Compound 3 C C 11 ComparativeExample Comparative Compound 4 C C 12 Example C1 Compound No O-10-10 A BExample C2 Compound No O-10-22 A A Example C3 Compound No N-11-4 B AExample C4 Compound No O-11-13 A A Example C5 Compound No O-12-42 A BExample C6 Compound No N-13-24 B A Example C7 Compound No S-13-18 A AExample C8 Compound No O-14-79 A A Example C9 Compound No S-15-16 B BExample C10 Compound No O-16-9 A A

From Tables 66 to 68 above, it can be seen that the organicelectroluminescent element using the host material of the presentinvention has excellent durability and low driving voltage, which isthus good.

REFERENCE SIGNS LIST

-   -   2 . . . SUBSTRATE    -   3 . . . ANODE    -   4 . . . HOLE INJECTING LAYER    -   5 . . . HOLE TRANSPORTING LAYER    -   6 . . . LIGHT EMITTING LAYER    -   7 . . . HOLE BLOCKING LAYER    -   8 . . . ELECTRON TRANSPORTING LAYER    -   9 . . . CATHODE    -   10 . . . ORGANIC ELECTROLUMINESCENT ELEMENT (ORGANIC EL ELEMENT)    -   11 . . . ORGANIC LAYER    -   12 . . . PROTECTIVE LAYER    -   14 . . . ADHESIVE LAYER    -   16 . . . SEALING ENCLOSURE    -   20 . . . LIGHT EMITTING DEVICE    -   30 . . . LIGHT SCATTERING MEMBER    -   30A . . . LIGHT INCIDENT SURFACE    -   30B . . . LIGHT OUTPUTTING SURFACE    -   31 . . . TRANSPARENT SUBSTRATE    -   32 . . . FINE PARTICLES    -   40 . . . ILLUMINATION DEVICE

1. An organic electroluminescent element comprising: a substrate; a pairof electrodes including an anode and a cathode, disposed on thesubstrate; and at least one organic layer including a light emittinglayer, disposed between the electrodes, wherein at least one layer ofthe organic layer(s) contains a compound represented by the followinggeneral formula (1):

wherein X¹ to X¹¹ each independently represents CR⁰ or N independently,and R⁰s each independently represents a hydrogen atom or a substituent;adjacent two of X¹ to X¹¹ each independently represents at least CR⁰,R⁰s of the adjacent two CR⁰s are bonded to each other to form a ring,and only one R⁰ of the adjacent two CR⁰s represents an aryl group or aheteroaryl group; provided that, in the case where X⁷ and X⁸ eachindependently represents CR⁰, R⁰ contained in X⁷ and R⁰ contained in X⁸are not bonded to each other to form a ring.
 2. The organicelectroluminescent element according to claim 1, wherein in the generalformula (1), one R⁰ of the adjacent two CR⁰s, in which R⁰s are bonded toeach other to form a ring, represent an aryl group or a heteroaryl groupof a 6-membered ring.
 3. The organic electroluminescent elementaccording to claim 1, wherein the compound represented by the generalformula (1) is a compound represented by any one of the followinggeneral formulae (2) to (9):

wherein Y^(A1) to Y^(H1) each independently represents CR¹R², NR³, O, S,or Se, R¹ to R³ each independently represents a substituent, X^(A1) toX^(A11), X^(B1) to X^(B15), X^(C1) to X^(C15), X^(D1) to X^(D15), X^(E1)to X^(E15), X^(F1) to X^(F15), X^(G1) to X^(G15) and X^(H1) to X^(H15)each independently represents CR⁴ or N, and CR⁴s each independentlyrepresents a hydrogen atom or a substituent.
 4. The organicelectroluminescent element according to claim 1, wherein the compoundrepresented by the general formula (1) is a compound represented by anyone of the following general formulae (10) to (17):

wherein Y^(A1) to Y^(H1) each independently represents CR¹R², NR³, O, S,or Se, and R¹ to R³ each independently represents a substituent; R^(A1)to R^(A15), R^(B1) to R^(B15), R^(C1) to R^(C15), R^(D1) to R^(D15),R^(E1) to R^(E15), R^(F1) to R^(F15), R^(G1) to R^(G15) and R^(H1) toR^(H15) each independently represents a hydrogen atom or a substituent.5. The organic electroluminescent element according to claim 1, whereinthe value of LUMO of the compound represented by the general formula(1), as determined by an electron density functional theory (B3LYP/6-31G(d) level), is more than 1.25.
 6. The organic electroluminescent elementaccording to claim 1, wherein the compound represented by the generalformula (1) has a substituent containing at least one of a pyridinering, a pyrimidine ring, a triazine ring, a cyano group, and a carbonylgroup.
 7. The organic electroluminescent element according to claim 1,wherein the light emitting layer contains at least one kind ofphosphorescent light emitting material.
 8. The organicelectroluminescent element according to claim 1, wherein thephosphorescent light emitting material is an iridium complex representedby the following general formula (E-1):

wherein Z¹ and Z² each independently represents a carbon atom or anitrogen atom; A¹ represents an atomic group that forms a 5- or6-membered hetero ring together with Z¹ and a nitrogen atom; B¹represents an atomic group that forms a 5- or 6-membered ring togetherwith Z² and a carbon atom; (X—Y) represents a mono-anionic bidentateligand; and n_(E1) represents an integer of 1 to
 3. 9. The organicelectroluminescent element according to claim 8, wherein the iridiumcomplex represented by the general formula (E-1) is represented by thefollowing general formula (E-2):

wherein A^(E1) to A^(E8) each independently represents a nitrogen atomor C—R^(E); R^(E) represents a hydrogen atom or a substituent; (X—Y)represents a mono-anionic bidentate ligand; and n_(E2) represents aninteger of 1 to
 3. 10. The organic electroluminescent element accordingto claim 1, wherein the light emitting layer contains the compoundrepresented by the general formula (1.
 11. A light emitting device usingthe organic electroluminescent element according to claim
 1. 12. Adisplay device using the organic electroluminescent element according toclaim
 1. 13. An illumination device using the organic electroluminescentelement according to claim
 1. 14. A compound represented by thefollowing general formula (1):

wherein X¹ to X¹¹ each independently represents CR⁰ or N, and R⁰s eachindependently represents a hydrogen atom or a substituent; adjacent twoof X¹ to X¹¹ each independently represents at least CR⁰, R⁰s of theadjacent two CR⁰s are bonded to each other to form a ring, and only oneR⁰ of the adjacent two CR⁰s represents an aryl group or a heteroarylgroup; provided that, in the case where X⁷ and X⁸ each independentlyrepresents CR⁰, R⁰ contained in X⁷ and R⁸ contained in X⁸ are not bondedto each other to form a ring.
 15. The compound according to claim 14,which is represented by any one of the following general formulae (2) to(9):

wherein Y^(A1) to Y^(H1) each dependently represents CR¹R², NR³, O, S,or Se, and R¹ to R³ each independently represents a substituent; X^(A1)to X^(A15), X^(B1) to X^(B15), X^(C1) to X^(C15), X^(D1) to X^(D15),X^(E1) to X^(E15), X^(F1) to X^(F15), X^(G1) to X^(G15) and X^(H1) toX^(H15) each independently represents CR⁴ or N, and CR⁴s eachindependently represents a hydrogen atom or a substituent.
 16. Thecompound according to claim 14, which is represented by any one of thefollowing general formulae (10) to (17):

wherein Y^(A1) to Y^(H1) each independently represents CR¹R², NR³, O, S,or Se, and R¹ to R³ each independently represents a substituent; R^(A1)to R^(A15), R^(B1) to R^(B15), R^(C1) to R^(C15), R^(D1) to R^(D15),R^(E1) to R^(E15), R^(F1) to R^(F15), R^(G1) to R^(G15) and R^(H1) toR^(H15) each independently represents a hydrogen atom or a substituent.17. A material for an organic electroluminescent element, represented bythe following general formula (1):

X¹ to X¹¹ each independently represents CR⁰ or N, and R⁰s eachindependently represents a hydrogen atom or a substituent; adjacent twoof X¹ to X¹¹ each independently represents at least CR⁰, R⁰s of theadjacent two CR⁰s are bonded to each other to form a ring, and only oneR⁰ of the adjacent two CR⁰s represents an aryl group or a heteroarylgroup; provided that, in the case where X⁷ and X⁸ each independentlyrepresents CR⁰, R⁰ contained in X⁷ and R⁰ contained in X⁸ are not bondedto each other to form a ring.
 18. The material for an organicelectroluminescent element according to claim 17, which is representedby any one of the following general formulae (2) to (9):

wherein Y^(A1) to Y^(H1) each independently represents CR¹R², NR³, O, S,or Se, and R¹ to R³ each independently represents a substituent; X^(A1)to X^(A15), X^(B1) to X^(B15), X^(C1) to X^(C15), X^(D1) to X^(D15),X^(E1) to X^(E15), X^(F1) to X^(F15), X^(G1) to X^(G15) and X^(H1) toX^(H15) each independently represents CR⁴ or N, and CR⁴s eachindependently represents a hydrogen atom or a substituent.
 19. Thematerial for an organic electroluminescent element according to claim17, which is represented by any one of the following general formulae(10) to (17):

wherein Y^(A1) to Y^(H1) each independently represents CR¹R², NR³, O, S,or Se, and R¹ to R³ each independently represents a substituent; R^(A1)to R^(A5), R^(B1) to R^(B15), R^(C1) to R^(C15), R^(D1) to R^(D15),R^(E1) to R^(E15), R^(F1) to R^(F15), R^(G1) to R^(G15) and R^(H1) toR^(H15) each independently represents a hydrogen atom or a substituent.